Herbicidal pyridine sulfonamides

ABSTRACT

(Aminosulfonyl)pyridine carboxamides are useful as agricultural chemicals. In particular, many compounds are useful as herbicides which show significant herbicidal activity on grasses and yet have the unexpected property of being safe to corn.

This application is a continuation of application Ser. No. 07/408,223,filed Sept. 15, 1989, now abandoned, which is a division of copendingapplication Ser. No. 07/234,640, filed Aug. 22, 1988, which is adivision of application Ser. No. 07/088,259, filed Aug. 24, 1987, nowU.S. Pat. No. 4,786,734, which is a continuation-in-part of applicationSer. No. 07/084,532, filed Aug. 12, 1987, now abandoned, which is acontinuation-in-part of application Ser. No. 06/936,105, filed Nov. 28,1987, now U.S. Pat. No. 4,789,393, which is a continuation-in-part ofapplication Ser. No. 06/837,392 filed Mar. 7, 1986, now abandoned.

BACKGROUND OF THE INVENTION

This invention relates to novel (aminosulfonyl)-pyridinecarboxamides.The compounds of this invention and their agriculturally suitable saltsare useful as agricultural chemicals, and in particular, as herbicideswhich may be selective to corn.

U.S. Pat. No. 4,544,401 and U.S. Pat. No. 4,435,206 disclose herbicidalpyridinesulfonylureas.

U.S. Pat. No. 4,518,776 (Swiss priority 7/19/82) and EP-A-101,670 (SwissPriority 8/23/82, published 2/29/84) disclose, in part, a process forthe preparation of compounds of formula ##STR1## wherein ##STR2##

R₁ is, among other values, C(O)NHC₁ -C₄ alkyl or C(O)N(C₁ -C₄ alkyl)₂ ;

R₂ is H, halogen, CF₃, NO₂, C₁ -C₄ alkyl or C₁ -C₄ alkoxy;

A is O, S, NR₅ or --C=N--;

X is C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₁ -C₄ alkoxy, C₁ -C₄ alkylthio, C₁-C₄ haloalkoxy, C₁ -C₄ alkylamino or di-C₁ -C₄ alkylamino;

Y is C₁ -C₄ alkyl, C₁ -C₄ alkoxy or C₁ -C₄ haloalkoxy; and

Z is CH or N. U.S. Pat. No. 4,518,776 generically discloses but does notclaim compounds of the invention. (No pyridine carboxamides arespecifically disclosed.)

U.S. Pat. No. 4,521,597 discloses, in part, a process for thepreparation of compounds of formula ##STR3##

R₃ is H, halogen, NO₂, OCH₃ or CF₃ ;

R₅ is, among others, CONR₈ R₉ ;

R₈ is H, C₁ -C₅ alkyl, C₁ -C₅ cyanoalkyl, OCH₃, OC₂ H₅ or C₃ -C₅alkenyl;

R₉ is H, C₁ -C₅ alkyl or C₃ -C₅ alkenyl;

Y is O, S or C(R₆)=N;

R_(a) is H, halogen, C₁ -C₅ alkyl, C₁ -C₅ haloalkyl,

C₁ -C₅ alkoxy, C₁ -C₅ haloalkoxy, C₁ -C₅ alkylthio, C₂ -C₁₀ alkoxyalkylor C₂ -C₁₀ alkoxyalkoxy;

R_(b) is the same as R_(a) or NR_(c) R_(d) ; and

E is CH or N.

This application generically discloses but does claim compounds of theinvention. (No pyridine carboxamides are specifically disclosed.)

U.S. Pat. No. 4,549,898 discloses herbicidal sulfonylureas of formula##STR4## wherein

X is O, S, NR₄ or C(R₅)=N;

Y is O or S;

Z is O or S;

E is N or CH;

R₁ is H, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₁ -C₄ haloalkoxy, C₁ -C₄alkoxy, halogen, C₁ -C₄ alkylthio, NR₆ R₇ or alkoxyalkyl containing notmore than 4 carbon atoms;

R₂ is, among others, CONR₆ R₇ ;

R₃ is H, halogen, C₁ -C₃ alkyl, OCH₃ or CF_(3;)

R₅ is H, NO₂, F, Cl, Br, CH₃, CF₃, S(O)_(n) C₁ -C₃ alkyl, COC₁ -C₄alkoxy or C₁ -C₃ alkoxy;

R₆ is H, C₁ -C₆ alkyl, C₁ -C₄ cyanoalkyl, methoxy or ethoxy; and

R₇ is H, C₁ -C₆ alkyl or C₃ -C₆ alkenyl.

EP-A-155,767, published 9/25/85, discloses, in part, herbicidalsulfonylureas of formula ##STR5## wherein

R is H or CH_(3;)

R₅ is H, CH₃, Cl, Br, CO₂ R₁₅, C(O)NR₁₆ R₁₇,

SO₂ NR₁₆ R₁₇, SO₂ N(OCH₃)CH₃, SO₂ R₁₈ or NO₂ ;

R₁₆ is C₁ -C₂ alkyl;

R₁₇ is C₁ -C₂ alkyl;

R₁₉ is CH₃, Cl, Br, NO₂, C₁ -C₂ alkylthio or C₁ -C₂ alkylsulfonyl;

X is CH₃, OCH₃, Cl, Br, OCH₂ CF₃ or OCHF₂ ;

Y is C₁ -C₃ alkyl, CH₂ F, cyclopropyl, C≡CH, OCH₃, OC₂ H₅, CH₂ OCH₃, NH₂NHCH₃, N(CH₃)₂, OCH₂ CH₂ F, CF₃, SCH₃, OCH₂ CH=CH₂, OCH₂ C≡CH, ##STR6##CR(OCH₂ CH₃)₂ or OCF₂ H; and

Z is CH or N.

Despite the existence of these materials, there is still a need forimproved agricultural chemicals, especially herbicides which may beselective for corn. According to this invention, such herbicides haveunexpectedly been found.

SUMMARY OF THE INVENTION

This invention comprises novel compounds of Formula I, agriculturallysuitable compositions containing them, and their method-of-use aspreemergent and/or postemergent herbicides or plant growth regulants.##STR7##

R is H or CH₃ ;

R₁ is H or C₁ -C₃ alkyl;

R₂ is C₁ -C₃ alkyl or C₁ -C₂ alkoxy; or

R₁ and R₂ may be taken together to form --(CH₂)n--, wherein n is 2, 3 or4;

R₃ is H, Cl, F, Br, CH₃, CF₃, OCH₃, OCH₂ CH₃ ; OCF₂ H, SCH₃, SCH₂ CH₃,SCF₂ H, NHR₄ or NR₄ R₅ ;

R₄ is CH₃ or CH₂ CH₃ ;

R₅ is CH₃, CH₂ CH₃, OCH₃ or OCH₂ CH₃ ; and

X is CH₃, CH₂ F, CH₂ CH₃, OCH₃, OCH₂ CH₃, Cl or CH₂ OCH₃.

Preferred for reasons of their greater herbicidal activity and/or morefavorable ease of synthesis are:

(1) Compounds of Formula I where R is H.

(2) Compounds of Preferred 1 where J is J-1.

(3) Compounds of Preferred 1 where J is J-2.

(4) Compounds of Preferred 1 where J is J-3.

(5) Compounds of Preferred 1 where J is J-4.

(6) Compounds of Preferred 2 where X is OCH₃, CH₃ or Cl.

(7 ) Compounds of Preferred 6 where R₃ is H, F, Cl, OCH₃, N(CH₃)₂ orSCH₃.

(8 ) Compounds of Preferred 7 where R₁ is H or CH₃ ; and R₂ is CH₃, CH₂CH₃ or OCH₃.

(9) Compounds of Preferred 3 where X is OCH₃, CH₃ or Cl.

(10) Compounds of Preferred 9 where R₃ is H, F, Cl, OCH₃, N(CH₃)₂ orSCH₃.

(11) Compounds of Preferred 10 where R₁ is H or CH₃ ; and R₂ is CH₃, CH₂CH₃ or OCH₃.

(12) Compounds of Preferred 4 where X is OCH₃, CH₃ or Cl.

(13) Compounds of Preferred 12 where R₃ is H, F, Cl, OCH₃, N(CH₃)₂ orSCH₃.

(14) Compounds of Preferred 13 where R₁ is H or CH₃ ; and R₂ is CH₃, CH₂CH₃ or OCH₃.

(15) Compounds of Preferred 5 where X is OCH₃, CH₃ or Cl.

(16) Compounds of Preferred 15 where R₃ is H, F, Cl, OCH₃, N(CH₃)₂ orSCH₃.

(17) Compounds of Preferred 16 where R₁ is H or CH₃ ; and R₂ is CH₃, CH₂CH₃ or OCH₃.

Specifically preferred for its greatest herbicidal activity withconcurrent safety to corn and/or more favorable ease of synthesis is:

2[[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]aminosulfonyl]-N,N-dimethyl-3-pyridinecarboxamide,m.p. 142°-159° C.(dec).

This invention also includes novel synthetic intermediates for thepreparation of the compounds of Formula I described in Examples 1-12below.

DETAILS OF THE INVENTION

Compounds of Formula I can be prepared by the methods described inEquations 1 and 2. ##STR8##

The reaction shown in Equation 1 is carried out by contacting the phenylcarbamate of Formula (3) with the aminoheterocycle of Formula (2) in aninert organic solvent such as dioxane or tetrahydrofuran at temperaturesof about 20° to 100° C. for a period of about one-half to twenty-fourhours. The product can be isolated by evaporation of the reactionsolvent and purified by trituration of the evaporation residue withsolvents such as 1-chlorobutane or ethyl ether and filtration, byrecrystallization from mixtures of solvents such as 1,2-dichloroethane,1-chlorobutane and heptane or by chromatography on silica gel.

The phenyl carbamates of Formula (3) can be prepared by the reaction ofa sulfonamide of Formula (4), Equation 2, with diphenylcarbonate in thepresence of a base (for example, aqueous potassium carbonate or sodiumhydroxide) as described in EPO 44,808 or South African PatentApplication No. 825042 (or modifications thereof). ##STR9##

The reaction of Equation 2 can be carried out by contacting equimolaramounts of the sulfonamide of Formula (4) with a heterocyclic phenylcarbamate of Formula (5) in the presence of an equimolar amount of1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), by methods analogous to thosedescribed in South African Patent Application No. 830441. The phenylcarbamates of Formula (5) can be prepared by methods (or modificationsthereof) described in South African Patent Application No. 825671 andSouth African Patent Application No. 825045 by reactingphenylchloroformate with the corresponding amino pyrimidine.

The sulfonamides of Formula (4) can be prepared by the methods shown inEquations 3, 4, 5, and 6.

Halopyridine-carboxylic acid derivatives of Formula (6) (Equation 3) canbe prepared by methods known in the art or modifications thereof such asthose described by S. G. Woods et al., J. Heterocvclic Chem., Vol. 21,p. 97 (1984) by L. Testaferri et al., in Tetrahedron, Vol. 41, p. 1373(1975) and in The Chemistry of Heterocyclic Compounds: Pyridine and ItsDerivatives, Vol. 14, Interscience Publishers, Inc., New York.

Compound (6) is treated with potassium benzylthiolate inN,N-dimethylformamide (DMF) at temperatures of about 100° to 150° C. fora period of about two hours as described by S. G. Woods et al. (op.cit.). The product (7) can be isolated by acidification and filtration.

The acid (7) is converted to amide (9) by treatment with excessthionylchloride and amination with two moles of dialkylamine in an inertorganic solvent, for example, tetrahydrofuran, methylene chloride orethyl acetate. The product (9) can be isolated by evaporation of thereaction solvent.

The reaction shown in Equation 3(d) is carried out by contacting sulfide(9) with sodium hypochlorite in an aqueous solution of hydrochloric acidusing procedures which are known in the art such as those disclosed inSouth African Patent Application No. 84/8844 or by treatment of (9) withchlorine in an aqueous solution of sodium chloride and sodiumbicarbonate. The sulfonyl chloride is converted to sulfonamide (4) bycontact with ammonia. The product can be isolated by evaporation of thesolvent.

Compound (7a), where the benzylthio group is in the ortho positionrelative to the pyridine nitrogen, can also be prepared by alkylation ofthe orthomercaptopyridine (6a) with a benzyl halide in the presence of abase, for example, sodium hydroxide. ##STR10##

Halopyridinethiol derivatives of Formula (11) (Equation 4) can beprepared by methods known in the art or modifications thereof such asthose described in U.S. Pat. No. 2,456,258 and by Grassetti et al. in J.Chromatography, Vol. III, p. 121 (1969) or from the halopyridin-4-ols asdescribed in Den Hertog et al. in Rec. Trav. Chim., Vol. 70, p. 353(1951) and M. S. Newman and H. A. Karnes, in J. Org. Chem., Vol. 31, p.410 (1966). The reaction shown in Equation 4a is carried out bycontacting thiol (11) with sodium hypochlorite according to theprocedure of L. H. McKendry et al. (op. cit.). Treatment of thesulfonamide (12) with potassium cyanide using methods described byTestaferri et al. (op. cit.) and hydrolysis with sodium hydroxide andhydrogen peroxide (March, Advanced Organic Chemistry, 3rd Edition, pp.809-810, McGraw-Hill, Inc., New York, 1977) gives acid (13). The acid isconverted to amide (4) by contact with thionyl chloride and aminationwith two moles of dialkylamine. The product can be isolated byevaporation of the solvent. ##STR11##

Diazonium derivatives of Formula (14) (Equation 5) can be prepared bymethods known in the art or by modifications thereof such as thosedescribed by Blanz et al. in J. Med. Chem., Vol. 6, p. 185 (1963). Thereaction shown in Equation 5a is carried out by contacting diazoniumsalt (14) with benzylthiol. Conversion of the acid (15) to amide (16) isaccomplished by treatment with thionyl chloride and amination with twomoles of dialkylamine. Reaction 5c is carried out according to theprocedure of L. H. McKendry et al. (op. cit.) to give sulfonamide (4).##STR12##

Pyridinesulfonyl halides of Formula (17) (Equation 6) can be preparedfrom the corresponding thiols, sulfides or sulfonic acids by methodsknown in the art, including those described above, or modificationsthereof. The reaction shown in Equation 6a is carried out by contactingsulfonyl halide (17) with tert-butylamine. The ortho-carboxamide (19) isprepared from (18) by a modification of the method described byQueguiner in Synthesis. p. 822 (1983). The tert-butylsulfonamide (19) isconverted to amide (4) by contact with trifluoroacetic acid. ##STR13##

The sulfonamide (19) (Equation 6) is also available by the route ofEquation 7. The pyridine ester (20) can be prepared by contacting acidchloride (8) with an alcohol (R_(x) is alkyl, aryl or arylalkyl).Sulfonyl chloride (21) is then obtained by treating (20) with sodiumhypochlorite in an aqueous solution of hydrochloric acid usingprocedures which are known in the art, such as those disclosed in SouthAfrican Patent Application No. 848844. The sulfonyl chloride (21) isconverted to the sulfonamide (22) by reaction with t-butylamine. Amide(19) is obtained by contacting (22) with the appropriate amine. Theproduct is isolated by evaporation of the solvent. ##STR14##

The acids (7) (Equation 3) can also be prepared as described in Equation8. Contacting pyridine carboxylic acids (23) with thionyl chlorideaffords acid chloride (24). Amide (25) is obtained upon treatment of(24) with an aromatic amine. Sulfide (26) is then prepared from (25) bya modification of the method of Epsztajn, et al. Tetrahedron Letters1983, 4735. Carboxylic acid (7) is prepared from (26) by basehydrolysis. The product is isolated by acidification.

The heterocyclic amines of Formula (2) are known compounds. ##STR15##For a review of the synthesis and reactions of 2-aminopyrimidines seeThe Chemistry of Heterocyclic Compounds, Vol. 16, Wiley-Interscience,New York (1962).

Agriculturally suitable salts of compounds of Formula I are also usefulherbicides and can be prepared by well-known methods including thosedescribed in U.S. Pat. No. 4,127,405.

The following Examples illustrate syntheses of the compounds of thisinvention. Temperatures are in degrees Celsius.

EXAMPLE 1 N,N-Dimethyl-2-(phenylmethylthio)-3-pyridinecarboxamide

A solution of 25.0 g (223 mmol) of potassium t-butoxide in 100 ml ofdimethylformamide was cooled to 0° C. and 22 ml (186 mmol) of benzylmercaptan added dropwise at 0° C. After addition was complete, thereaction mixture was allowed to warm to 25° C. and stirred at thistemperature for 15 minutes. The reaction mixture was then re-cooled to0° C. and 34.0 g (186 mmol) ofN,N-dimethyl-2-(chloro)-3-pyridinecarboxamide added in one portion.After an exotherm to 50° C, the mixture was heated at 80° C. for 1.5hour. The mixture was cooled, poured into 100 ml of water and extractedwith ether. The combined organic extracts were washed twice with water,then brine and dried over sodium sulfate. Concentration gave 19.2 g of aviscous yellow oil. IR (Nujol) 1640 (CONMe₂) cm⁻¹.

NMR (CDCl₃): δ6 2.72 (s, 3H, NCH₃);

3.04 (s, 3H, NCH₃);

4.49 (s, 2H, SCH₂ C₆ H₅);

6.97-7.17 (m, 1H);

7.18-7.57 (m, 6H); and

8.50 (d of d, 1H).

EXAMPLE 2 N,N-Dimethyl-2-aminosulfonyl-3-pyridinecarboxamide

A mixture of 4.4 ml of concentrated hydrochloric acid, 66 ml ofmethylene chloride, 34 ml of water and 4.0 g (14.7 mmol) of theN,N-dimethyl-2-(phenylmethylthio)-3-pyridinecarboxamide was cooled to 0°C. Maintaining a temperature of -5° to 3° C., 60 m of 5% sodiumhypochlorite was added dropwise over 15 minutes. The resulting yellowemulsion was stirred at 0° C. an additional 20 minutes. The reactionmixture was then poured into water and extracted with methylenechloride. The combined organic extracts were kept at 0° C. and washedwith a saturated sodium bisulfite solution and dried over sodiumsulfate. After 30 minutes, the yellow solution was filtered into areaction flask and cooled to -78° C. and 5 ml (431 mmol) of dry ammoniaadded. The reaction mixture was allowed to warm to room temperature andthe solvent removed under reduced pressure. The resulting solid wasslurried with 5 ml of water and the insoluble white solid collected byfiltration to provide 2.0 g of the subject compound, m.p. 198°-209°C.(d).

NMR (DMSO): δ2.70 (s, 3H, NCH₃);

2.93 (s, 3H, NCH₃);

7.60-7.75 (m, 1H);

7.90 (m, 1H); and

8.75 (m, 1H).

EXAMPLE 3 N,N-Dimethyl-2-[[(4,6-dimethoxypyrimidin-2-yl)amino-carbonyl]aminosulfonyl]-3-pyridinecarboxamide

To a suspension of .50 g (2.2 mmol)N,N-dimethyl2-(aminosulfonyl)-3-pyridinecarboxamide and .60 g (2.2 mmol)of 4,6-dimethoxypyrimidin-2-yl phenyl carbamate in 3 ml acetonitrile wasadded .32 ml (2.2 mmol) of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU). Theresulting solution was stirred at room temperature for 7 minutes. Theaddition of 6 ml of water followed by the dropwise addition of 10%hydrochloric acid produced a white precipitate which was collected byfiltration to provide .75 g of the subject compound, m.p. 142°-159°C.(d). IR (Nujol) 1720 (CO), 1609, 1365, 1162 cm⁻¹.

NMR (DMSO): δ2.80 (s, 3H, NCH₃);

2.93 (s, 3H, NCH₃);

3.89 (s, 6H, OCH₃);

6.02 (s, 1H);

7.70-7.80 (m, 1H);

8.00 (m, 1H);

8.72 (m, 1H);

10.62 (s, 1H, NH); and

12.75 (s, 1H, NH).

EXAMPLE 4 2-(Phenylmethylthio)-3-pyridinecarboxylic acid

200 parts 2-mercaptonicotinic acid, 970 parts of water, 215 parts of 50%NaOH, and 164 parts of benzyl chloride were combined and the resultingsolution was refluxed for 2 hours. After dilution with 2580 parts ofwater, the solution was acidified with 207 parts of 36% HCl. Theresulting slurry was cooled and filtered. The wet cake was washed withwater and dried to give 307 parts (97.1%) of2-(phenylmethylthio)-3-pyridinecarboxylic acid, m.p. 190°-193° C.

EXAMPLE 5 N,N-Dimethyl-2-(phenylmethylthio)-3-pyridinecarboxamide

A mixture of 29.7 parts of thionylchloride, 50.0 parts of2-(phenylmethylthio)-3-pyridinecarboxylic acid, and 225 parts of ethylacetate was refluxed for 1.6 hours. The resulting solution of2-(phenylmethylthio)-3-pyridinecarbonyl chloride was cooled to 5° C.While maintaining the temperature at approximately 10° C, 70 parts of40% dimethylamine in water were added. The PH was adjusted to 4.0 with36% HCl and the lower aqueous layer was decanted. Water was added to theethyl acetate layer and the resulting mixture was distilled until theethyl acetate was removed. After cooling and seeding,N,N-dimethyl-2-(phenylmethylthio)-3-pyridinecarboxamide was recovered byfiltration, washed with water, and dried. This gave 52.1 parts (93.9%),melting point 61°-63° C.

EXAMPLE 6 2-(Chlorosulfonyl)-N.N dimethyl-3-pyridinecarboxamide

A mixture of 60 partsN,N-dimethyl-2-(phenyl-methylthio)-3-pyridinecarboxamide, 240 parts ofwater, and 372 parts of Freon® TF was kept at 2° C. by external coolingwhile 59 parts of Cl₂ was passed in during 10 minutes. The solids thatformed were collected by filtration, washed with ice water (2×100 parts)and Freon® TF (2×55 parts), and dried by drawing dry air through thefilter. This gave 46.7 parts (85.2% yeild) of3-((dimethylamino)carbonyl))-2-pyridinesulfonyl chloride, melting point110°-114° C. If this material is to be kept for any length of time, itshould be stored at <0° C.

EXAMPLE 7 2-(Chlorosulfonyl)-N,N-dimethyl-3-pyridinecarbonamide

A mixture of N,N dimethyl-2-(phenylmethylthio)3-pyridinecarboxamide (1mole as a 12-15% solution in CH₂ Cl₂), sodium bicarbonate (2.15 mole),sodium chloride (9.25 mole) and water (2.4 L) was cooled to 0° C.Chlorine (3 moles) was fed into the reaction mixture over 1 hour whilemaintaining the temperature at 0° C. Excess chlorine was then quenchedby addition of 10% aqueous sodium bisulfite. The layers were separatedand the aqueous phase extracted with additional methylene chloride. Thecombined organic solutions containing the sulfonyl chloride product werestored at 0° C.

EXAMPLE 8 2-(Aminosulfonyl)-N,N-dimethyl-3-pyridinecarboxamide

Anhydrous NH₃ (9 parts) was sparged into a mixture of 45.0 parts ofsulfonyl chloride and 120 parts of THF. The NH₃ addition required 40minutes during which time the temperature was kept below 10° C. Water(115 parts) was added and the pH was adjusted to 7.5 with 13 parts of36% HCl. The resulting mixture was then distilled until the pottemperature reached 0 79° C. After cooling, the product was collected byfiltration, washed with cold water, and dried. This gave 32.4 parts(78.2%) of 2-(aminosulfonyl)-N,N-dimethyl-3-pyridinecarboxamide, meltingpoint 188°-191° C.

EXAMPLE 9 2-(Aminosulfonyl)-N,N-dimethyl-3-pyridinecarboxamide

The solution of Example 7 was added to a mixture of 14% aqueous ammoniumhydroxide (3 mole) in 4 times the volume of methylene chloride over 30minutes at 20° C. After stirring an additional 15 minutes, sodiumhydroxide (1.85 mole as a 6% aqueous solution) was added to convert theproduct sulfonamide to its water soluble sodium salt. After 30 minutes,the layers were separated and the aqueous phase acidified to pH 2 withconcentrated hydrochloric acid. After stirring 1 hour at 0° C, themixture was filtered and the product washed with water and air dried.

EXAMPLE 10 Phenyl[3-[(N,N-dimethylaminocarbonyl)-2-pyridinyl]-sulfonyl]carbamate

Phenyl chloroformate (30.4 parts) was added over 25 minutes to a mixtureof 20.0 parts of 2-(aminosulfonyl)-N,N-dimethyl-3-pyridinecarboxamide,30.3 parts of 50% NaOH, and 63 parts of acetone. The temperature waskept between 0° and 5° C. After stirring for another 20 minutes, 157parts of water was added. The resulting thin slurry was filtered. Thefiltrate was acidified to PH 2 with 20 parts of 36% HCl. Theprecipitated solids were recovered by filtration, washed with water, anddried. This gave 26.3 parts (86.3%) of the phenyl ester of[3-[[(dimethylaminocarbonyl)-2-pyridinyl]sulfonyl]carbamic acid, m.p.150°-154° C.

EXAMPLE 11Phenyl[3-[(N,N-dimethylaminocarbonyl)-2-pyridinyl]-sulfonyl]carbamate

2-(Aminosulfonyl)-N,N-dimethyl-3-pyridinecarboxamide (1 mole), potassiumcarbonate (2.8 mole as a 50% aqueous solution), and acetone (900 mL)were combined and stirred at room temperature for 30 minutes to affordthe sulfonamide potassium salt. Phenyl chloroformate (1.4 mole) was thenadded over 30 minutes at 25°-30° C. to form a slurry of the potassiumsalt of the product. After stirring an additional hour, water (2.26 L)was added to dissolve the salt, the mixture was filtered to removeinsoluble diphenyl carbonate. The filtrate containing the salt of theproduct was then acidified to pH 2 with concentrated hydrochloric acidover 30 minutes at room temperature. The mixture was filtered and theproduct solid washed with water and air dried.

EXAMPLE 12 N,N-Dimethyl-2-[[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]aminosulfonyl]-3-pyridinecarboxamide

12.0 parts of the carbamate of Example 8, 5.33 parts of2-amino-4,6-dimethoxypyrimidine, and 36 parts of ethyl acetate wererefluxed for 1.0 hour. The slurry was cooled and filtered. The solidswere washed with ethyl acetate and dried to give 12.3 parts (87.3%yield) of the subject compound, m.p 184°-185° C.

The following compounds may be prepared by one skilled in the art usingthe procedures described earlier and exemplified in Examples 1-12.

                                      TABLE 1    __________________________________________________________________________     ##STR16##    R   r.sub.1 R.sub.2 R.sub.3 X      m.p. (°C)    __________________________________________________________________________    H   H       CH.sub.3                        H       OCH.sub.3                                       134-40    H   H       CH.sub.2 CH.sub.3                        H       OCH.sub.3                                       169-72    H   H       CH.sub.2 CH.sub.2 CH.sub.3                        H       OCH.sub.3    H   H       CH(CH.sub.3).sub.2                        H       OCH.sub.3    H   H       OCH.sub.3                        H       OCH.sub.3    H   H       OCH.sub.2 CH.sub.3                        H       OCH.sub.3    H   H       CH.sub.3                        CH.sub.3                                146-48    H   H       CH.sub.2 CH.sub.3                        H       CH.sub.3    H   H       CH.sub.2 CH.sub.2 CH.sub.3                        H       CH.sub.3    H   H       CH(CH.sub.3).sub.2                        H       CH.sub.3    H   H       OCH.sub.3                        H       CH.sub.3    H   H       OCH.sub.2 CH.sub.3                        H       CH.sub.3    H   H       CH.sub.3                        H       Cl     141-44    H   H       CH.sub.2 CH.sub.3                        H       Cl    H   H       CH.sub.2 CH.sub.2 CH.sub.3                        H       Cl    H   H       CH(CH.sub.3).sub.2                        H       Cl    H   H       OCH.sub.3                        H       Cl    H   H       OCH.sub.2 CH.sub.3                        H       Cl    H   H       CH.sub.3                        H       CH.sub.2 F    H   H       CH.sub.2 CH.sub.3                        H       CH.sub.2 F    H   H       OCH.sub.3                        H       CH.sub.2 F    H   H       CH.sub.3                        H       OCH.sub.2 CH.sub.3    H   H       CH.sub.2 CH.sub.3                        H       OCH.sub.2 CH.sub.3    H   H       OCH.sub.3                        H       OCH.sub.2 CH.sub.3    H   H       CH.sub.3                        H       CH.sub.2 OCH.sub.3    H   H       CH.sub.2 CH.sub.3                        H       CH.sub.2 OCH.sub.3    H   H       OCH.sub.3                        H       CH.sub.2 OCH.sub.3    CH.sub.3        H       CH.sub.3                        H       OCH.sub.3    CH.sub.3        H       OCH.sub.3                        H       OCH.sub.3    CH.sub.3        H       CH.sub.3                        H       CH.sub.3    CH.sub.3        H       OCH.sub.3                        H       CH.sub.3    CH.sub.3        H       CH.sub.3                        H       Cl    CH.sub.3        H       OCH.sub.3                        H       Cl    CH.sub.3        H       CH.sub.3                        H       CH.sub.2 F    CH.sub.3        H       CH.sub.3                        H       CH.sub.2 OCH.sub.3    H   CH.sub.3                CH.sub.3                        H       OCH.sub.3                                       142-159 d    H   CH.sub.3                CH.sub.2 CH.sub.3                        H       OCH.sub.3                                       123-125 d    H   CH.sub.3                CH.sub.2 CH.sub.2 CH.sub.3                        H       OCH.sub.3    H   CH.sub.3                CH(CH.sub.3).sub.2                        H       OCH.sub.3    H   CH.sub.3                OCH.sub.3                        H       OCH.sub.3                                       174-177 d    H   CH.sub.3                OCH.sub.2 CH.sub.3                        H       OCH.sub.3    H   CH.sub.3                CH.sub.3                        H       CH.sub.3                                       151-152 d    H   CH.sub.3                CH.sub.2 CH.sub.3                        H       CH.sub.3                                       133-134 d    H   CH.sub.3                CH.sub.2 CH.sub.2 CH.sub.3                        H       CH.sub.3    H   CH.sub.3                CH(CH.sub.3).sub.2                        H       CH.sub.3    H   CH.sub.3                OCH.sub.3                        H       CH.sub.3                                       130 d    H   CH.sub.3                OCH.sub.2 CH.sub.3                        H       CH.sub.3    H   CH.sub.3                CH.sub.3                        H       Cl     144-145 d    H   CH.sub.3                CH.sub.2 CH.sub.3                        H       Cl    H   CH.sub.3                CH.sub.2 CH.sub.2 CH.sub.3                        H       Cl    H   CH.sub.3                CH(CH.sub.3).sub.2                        H       Cl    H   CH.sub.3                OCH.sub.3                        H       Cl    H   CH.sub.3                OCH.sub.2 CH.sub.3                        H       Cl     118 d    H   CH.sub.3                CH.sub.3                        H       CH.sub.2 F    H   CH.sub.3                CH.sub.2 CH.sub.3                        H       CH.sub.2 F    H   CH.sub.3                OCH.sub.3                        H       CH.sub.2 F    H   CH.sub.3                CH.sub.3                        H       OCH.sub.2 CH.sub.3    H   CH.sub.3                CH.sub.2 CH.sub.3                        H       OCH.sub.2 CH.sub.3    H   CH.sub.3                OCH.sub.3                        H       OCH.sub.2 CH.sub.3    H   CH.sub.3                CH.sub.3                        H       CH.sub.2 OCH.sub.3    H   CH.sub.3                CH.sub.2 CH.sub.3                        H       CH.sub.2 OCH.sub.3    H   CH.sub.3                OCH.sub.3                        H       CH.sub.2 OCH.sub.3    CH.sub.3        CH.sub.3                CH.sub.3                        H       OCH.sub.3    CH.sub.3        CH.sub.3                OCH.sub.3                        H       OCH.sub.3    CH.sub.3        CH.sub.3                CH.sub.3                        H       CH.sub.3    CH.sub.3        CH.sub.3                OCH.sub.3                        H       CH.sub.3    CH.sub.3        CH.sub.3                CH.sub.3                        H       Cl    CH.sub.3        CH.sub.3                OCH.sub.3                        H       Cl    CH.sub.3        CH.sub.3                H       CH.sub.2 F    CH.sub.3        CH.sub.3                CH.sub.3                        H       CH.sub.2 OCH.sub.3    H   CH.sub.2 CH.sub.3                CH.sub.2 CH.sub.3                        H       OCH.sub.3                                       123-129 d    H   CH.sub.2 CH.sub.3                CH.sub.2 CH.sub.2 CH.sub.3                        H       OCH.sub.3    H   CH.sub.2 CH.sub.3                OCH.sub.3                        H       OCH.sub.3    H   CH.sub.2 CH.sub.3                CH.sub.2 CH.sub.3                        H       CH.sub.3                                       128-133 d    H   CH.sub.2 CH.sub.3                CH.sub.2 CH.sub.2 CH.sub.3                        H       CH.sub.3    H   CH.sub.2 CH.sub.3                OCH.sub.3                        H       CH.sub.3    H   CH.sub.2 CH.sub.3                CH.sub.2 CH.sub.3                        H       Cl     129-130 d    H   CH.sub.2 CH.sub.3                CH.sub.2 CH.sub.2 CH.sub.3                        H       Cl    H   CH.sub.2 CH.sub.3                OCH.sub.3                        H       Cl    H   CH.sub.2 CH.sub.3                CH.sub.2 CH.sub.3                        H       CH.sub.2 F    H   CH.sub.2 CH.sub.3                CH.sub.2 CH.sub.3                        H       OCH.sub.2 CH.sub.3    H   CH.sub.2 CH.sub.3                CH.sub.2 CH.sub.3                        H       CH.sub.2 OCH.sub.3    CH.sub.3        CH.sub.2 CH.sub.3                CH.sub.2 CH.sub.3                        H       OCH.sub.3    CH.sub.3        CH.sub.2 CH.sub.3                CH.sub.2 CH.sub.3                        H       CH.sub.3    CH.sub.3        CH.sub.2 CH.sub.3                CH.sub.2 CH.sub.3                        H       Cl    H   CH.sub.2 CH.sub.2 CH.sub.3                CH.sub.2 CH.sub.2 CH.sub.3                        H       OCH.sub.3    H   CH.sub.2 CH.sub.2 CH.sub.3                OCH.sub.3                        H       OCH.sub.3    H   CH.sub.2 CH.sub.2 CH.sub.3                CH.sub.2 CH.sub.2 CH.sub.3                        H       CH.sub.3    H   CH.sub.2 CH.sub.2 CH.sub.3                OCH.sub.3                        H       CH.sub.3    H   CH.sub.2 CH.sub.2 CH.sub.3                CH.sub.2 CH.sub.2 CH.sub.3                        H       Cl    H   CH.sub.2 CH.sub.2 CH.sub.3                OCH.sub.3                        H       Cl    H   CH(CH.sub.3).sub.2                CH(CH.sub.3).sub.2                        H       OCH.sub.3                                       146-162 d    H   H       CH.sub.3                        4-Cl    OCH.sub.3    H   H       OCH.sub.3                        4-Cl    OCH.sub.3    H   H       CH.sub.3                        5-Cl    OCH.sub.3    H   H       OCH.sub.3                        5-Cl    OCH.sub.3    H   H       CH.sub.3                        6-Cl    OCH.sub.3    H   H       OCH.sub.3                        6-Cl    OCH.sub.3    CH.sub.3        H       CH.sub.3                        6-Cl    OCH.sub.3    H   CH.sub.3                CH.sub.3                        4-Cl    OCH.sub.3    H   CH.sub.3                OCH.sub.3                        4-Cl    OCH.sub.3    H   CH.sub.3                CH.sub.3                        5-Cl    OCH.sub.3    H   CH.sub.3                OCH.sub.3                        5-Cl    OCH.sub.3    H   CH.sub.3                CH.sub.3                        6-Cl    OCH.sub.3                                       114-15    H   CH.sub.3                CH.sub.3                        6-Cl    Cl     169-72    H   CH.sub.3                OCH.sub.3                        6-Cl    OCH.sub.3    CH.sub.3        CH.sub.3                CH.sub.3                        6-Cl    OCH.sub.3    H   CH.sub.3                CH.sub.3                        4-Br    OCH.sub.3    H   CH.sub.3                CH.sub.3                        5-Br    OCH.sub.3    H   CH.sub.3                CH.sub.3                        6-Br    OCH.sub.3    H   CH.sub.3                CH.sub.3                        4-F     OCH.sub.3    H   CH.sub.3                CH.sub.3                        5-F     OCH.sub.3    H   CH.sub.3                CH.sub.3                        6-F     OCH.sub.3    H   CH.sub.3                CH.sub.3                        4-CH.sub.3                                OCH.sub.3    H   CH.sub.3                CH.sub.3                        5-CH.sub.3                                OCH.sub.3    H   CH.sub.3                CH.sub.3                        6-CH.sub.3                                OCH.sub.3                                       124-125 d    H   CH.sub.3                CH.sub.3                        6-CH.sub.3                                CH.sub.3                                       151-153    H   CH.sub.3                CH.sub.3                        4-OCH.sub.3                                OCH.sub.3    H   CH.sub.3                CH.sub.3                        5-OCH.sub.3                                OCH.sub.3    H   CH.sub.3                CH.sub.3                        6-OCH.sub.3                                OCH.sub.3    H   CH.sub.3                CH.sub.3                        6-OCH.sub.3                                CH.sub.3    H   CH.sub.3                CH.sub.3                        4-SCH.sub.3                                OCH.sub.3    H   CH.sub.3                CH.sub.3                        5-SCH.sub.3                                OCH.sub.3    H   CH.sub.3                CH.sub.3                        6-SCH.sub.3                                OCH.sub.3                                       195-98    H   CH.sub.3                CH.sub.3                        6-SCH.sub.3                                CH.sub.3                                       191-92 d    H   CH.sub.3                CH.sub.3                        6-SCH.sub.3                                Cl     170-73    H   CH.sub.3                CH.sub.3                        4-SCH.sub.2 CH.sub.3                                OCH.sub.3    H   CH.sub.3                CH.sub.3                        5-SCH.sub.2 CH.sub.3                                OCH.sub.3    H   CH.sub.3                CH.sub.3                        6-SCH.sub.2 CH.sub.3                                OCH.sub.3                                       180-84    H   CH.sub.3                CH.sub.3                        6-SCH.sub.2 CH.sub.3                                CH.sub.3                                       183-85    H   CH.sub.3                CH.sub.3                        6-SCH.sub.2 CH.sub.3                                Cl     165-72    H   CH.sub.3                CH.sub.3                        4-N(CH.sub.3).sub.2                                OCH.sub.3    H   CH.sub.3                CH.sub.3                        5-N(CH.sub.3).sub.2                                OCH.sub.3    H   CH.sub.3                CH.sub.3                        6-N(CH.sub.3).sub.2                                OCH.sub.3                                       192-93    H   CH.sub.3                CH.sub.3                        4-SCF.sub.2 H                                OCH.sub.3    H   CH.sub.3                CH.sub.3                        5-SCF.sub.2 H                                OCH.sub.3    H   CH.sub.3                CH.sub.3                        6-SCF.sub.2 H                                OCH.sub.3    H   CH.sub.3                CH.sub.3                        4-CF.sub.3                                OCH.sub.3    H   CH.sub.3                CH.sub.3                        5-CF.sub.3                                OCH.sub.3    H   CH.sub.3                CH.sub.3                        6-CF.sub.3                                OCH.sub.3    H   CH.sub.3                CH.sub.3                        4-OCF.sub.2 H                                OCH.sub.3    H   CH.sub.3                CH.sub.3                        5-OCF.sub.2 H                                OCH.sub.3    H   CH.sub.3                CH.sub.3                        6-OCF.sub.2 H                                OCH.sub.3    H   (CH.sub.2).sub.2                        H       OCH.sub.3    H   (CH.sub.2).sub.3                        H       OCH.sub.3                                       167-8    H   (CH.sub.2).sub.3                        H       CH.sub.3                                       138-39    H   (CH.sub.2).sub.3                        H       Cl     131-32    H   (CH.sub.2).sub.4                        H       OCH.sub.3                                       129 d    H   (CH.sub.2).sub.4                        H       CH.sub.3                                       140 d    H   (CH.sub.2).sub.4                        H       Cl     131-33    __________________________________________________________________________

                                      TABLE 2    __________________________________________________________________________     ##STR17##    R   R.sub.1 R.sub.2 R.sub.3 X      m.p. (°C)    __________________________________________________________________________        H       CH.sub.3                        H       OCH.sub.3    H   H       CH.sub.2 CH.sub.3                        H       OCH.sub.3    H   H       CH.sub.2 CH.sub.2 CH.sub.3                        H       OCH.sub.3    H   H       CH(CH.sub.3).sub.2                        H       OCH.sub.3    H   H       OCH.sub.3                        H       OCH.sub.3    H   H       OCH.sub.2 CH.sub.3                        H       OCH.sub.3    H   H       CH.sub.3                        H       CH.sub.3    H   H       CH.sub.2 CH.sub.3                        H       CH.sub.3    H   H       CH.sub.2 CH.sub.2 CH.sub.3                        H       CH.sub.3    H   H       CH(CH.sub.3).sub.2                        H       CH.sub.3    H   H       OCH.sub.3                        H       CH.sub.3    H   H       OCH.sub.2 CH.sub.3                        H       CH.sub.3    H   H       CH.sub.3                        H       Cl    H   H       CH.sub.2 CH.sub.3                        H       Cl    H   H       CH.sub.2 CH.sub.2 CH.sub.3                        H       Cl    H   H       CH(CH.sub.3).sub.2                        H       Cl    H   H       OCH.sub.3                        H       Cl    H   H       OCH.sub.2 CH.sub.3                        H       Cl    H   H       CH.sub.3                        H       CH.sub.2 F    H   H       CH.sub.2 CH.sub.3                        H       CH.sub.2 F    H   H       OCH.sub.3                        H       CH.sub.2 F    H   H       CH.sub.3                        H       OCH.sub.2 CH.sub.3    H   H       CH.sub.2 CH.sub.3                        H       OCH.sub.2 CH.sub.3    H   H       OCH.sub.3                        H       OCH.sub.2 CH.sub.3    H   H       CH.sub.3                        H       CH.sub.2 OCH.sub.3    H   H       CH.sub.2 CH.sub.3                        H       CH.sub.2 OCH.sub.3    H   H       OCH.sub.3                        H       CH.sub.2 OCH.sub.3    CH.sub.3        H       CH.sub.3                        H       OCH.sub.3    CH.sub.3        H       OCH.sub.3                        H       OCH.sub.3    CH.sub.3        H       CH.sub.3                        H       CH.sub.3    CH.sub.3        H       OCH.sub.3                        H       CH.sub.3    CH.sub.3        H       CH.sub.3                        H       Cl    CH.sub.3        H       OCH.sub.3                        H       Cl    CH.sub.3        H       CH.sub.3                        H       CH.sub.2 F    CH.sub.3        H       CH.sub.3                        H       CH.sub.2 OCH.sub.3    H   CH.sub.3                CH.sub.3                        H       OCH.sub.3                                       189-91    H   CH.sub.3                CH.sub.2 CH.sub.3                        H       OCH.sub.3    H   CH.sub.3                CH.sub.2 CH.sub.2 CH.sub.3                        H       OCH.sub.3    H   CH.sub.3                CH(CH.sub.3).sub.2                        H       OCH.sub.3    H   CH.sub.3                OCH.sub.3                        H       OCH.sub.3    H   CH.sub.3                OCH.sub.2 CH.sub.3                        H       OCH.sub.3    H   CH.sub.3                CH.sub.3                        H       CH.sub.3    H   CH.sub.3                CH.sub.2 CH.sub.3                        H       CH.sub.3    H   CH.sub.3                CH.sub.2 CH.sub.2 CH.sub.3                        H       CH.sub.3    H   CH.sub.3                CH(CH.sub.3).sub.2                        H       CH.sub.3    H   CH.sub.3                OCH.sub.3                        H       CH.sub.3    H   CH.sub.3                OCH.sub.2 CH.sub.3                        H       CH.sub.3    H   CH.sub.3                CH.sub.3                        H       Cl     173-75    H   CH.sub.3                CH.sub.2 CH.sub.3                        H       Cl    H   CH.sub.3                CH.sub.2 CH.sub.2 CH.sub.3                        H       Cl    H   CH.sub.3                CH(CH.sub.3).sub.2                        H       Cl    H   CH.sub.3                OCH.sub.3                        H       Cl    H   CH.sub.3                OCH.sub.2 CH.sub.3                        H       Cl    H   CH.sub.3                CH.sub.3                        H       CH.sub.2 F    H   CH.sub.3                CH.sub.2 CH.sub.3                        H       CH.sub.2 F    H   CH.sub.3                OCH.sub. 3                        H       CH.sub.2 F    H   CH.sub.3                CH.sub.3                        H       OCH.sub.2 CH.sub.3    H   CH.sub.3                CH.sub.2 CH.sub.3                        H       OCH.sub.2 CH.sub.3    H   CH.sub.3                OCH.sub.3                        H       OCH.sub.2 CH.sub.3    H   CH.sub.3                CH.sub.3                        H       CH.sub.2 OCH.sub.3    H   CH.sub.3                CH.sub.2 CH.sub.3                        H       CH.sub.2 OCH.sub.3    H   CH.sub.3                OCH.sub.3                        H       CH.sub.2 OCH.sub.3    CH.sub.3        CH.sub.3                CH.sub.3                        H       OCH.sub.3    CH.sub.3        CH.sub.3                OCH.sub.3                        H       OCH.sub.3    CH.sub.3        CH.sub.3                CH.sub.3                        H       CH.sub.3    CH.sub.3        CH.sub.3                OCH.sub.3                        H       CH.sub.3    CH.sub.3        CH.sub.3                CH.sub.3                        H       Cl    CH.sub.3        CH.sub.3                OCH.sub.3                        H       Cl    CH.sub.3        CH.sub.3                CH.sub.3                        H       CH.sub.2 F    CH.sub.3        CH.sub.3                CH.sub.3                        H       CH.sub.2 OCH.sub.3    H   CH.sub.2 CH.sub.3                CH.sub.2 CH.sub.3                        H       OCH.sub.3    H   CH.sub.2 CH.sub.3                CH.sub.2 CH.sub.2 CH.sub.3                        H       OCH.sub.3    H   CH.sub.2 CH.sub.3                OCH.sub.3                        H       OCH.sub.3    H   CH.sub.2 CH.sub.3                CH.sub.2 CH.sub.3                        H       CH.sub.3    H   CH.sub.2 CH.sub.3                CH.sub.2 CH.sub.2 CH.sub. 3                        H       CH.sub.3    H   CH.sub.2 CH.sub.3                OCH.sub.3                        H       CH.sub.3    H   CH.sub.2 CH.sub.3                CH.sub.2 CH.sub.3                        H       Cl    H   CH.sub.2 CH.sub.3                CH.sub.2 CH.sub.2 CH.sub.3                        H       Cl    H   CH.sub.2 CH.sub.3                OCH.sub.3                        H       Cl    H   CH.sub.2 CH.sub.3                CH.sub.2 CH.sub.3                        H       CH.sub.2 F    H   CH.sub.2 CH.sub.3                CH.sub.2 CH.sub.3                        H       OCH.sub.2 CH.sub.3    H   CH.sub.2 CH.sub.3                CH.sub.2 CH.sub.3                        H       CH.sub.2 OCH.sub.3    CH.sub.3        CH.sub.2 CH.sub.3                CH.sub.2 CH.sub.3                        H       OCH.sub.3    CH.sub.3        CH.sub.2 CH.sub.3                CH.sub.2 CH.sub.3                        H       CH.sub.3    CH.sub.3        CH.sub.2 CH.sub.3                CH.sub.2 CH.sub.3                        H       Cl    H   CH.sub.2 CH.sub.2 CH.sub.3                CH.sub.2 CH.sub.2 CH.sub.3                        H       OCH.sub.3    H   CH.sub.2 CH.sub.2 CH.sub.3                OCH.sub.3                        H       OCH.sub.3    H   CH.sub.2 CH.sub.2 CH.sub.3                CH.sub.2 CH.sub.2 CH.sub.3                        H       CH.sub.3    H   CH.sub.2 CH.sub.2 CH.sub.3                OCH.sub.3                        H       CH.sub.3    H   CH.sub.2 CH.sub.2 CH.sub.3                CH.sub.2 CH.sub.2 CH.sub.3                        H       Cl    H   CH.sub.2 CH.sub.2 CH.sub.3                OCH.sub.3                        H       Cl    H   CH(CH.sub.3).sub.2                CH(CH.sub.3).sub.2                        H       OCH.sub.3    H   H       CH.sub.3                        4-Cl    OCH.sub.3    H   H       OCH.sub.3                        4-Cl    OCH.sub.3    H   H       CH.sub.3                        5-Cl    OCH.sub.3    H   H       OCH.sub.3                        5-Cl    OCH.sub.3    H   H       CH.sub.3                        6-Cl    OCH.sub.3    H   H       OCH.sub.3                        6-Cl    OCH.sub.3    CH.sub.3        H       CH.sub.3                        4-Cl    OCH.sub.3    H   CH.sub.3                CH.sub.3                        4-Cl    OCH.sub.3    H   CH.sub.3                OCH.sub.3                        4-Cl    OCH.sub.3    H   CH.sub.3                CH.sub.3                        5-Cl    OCH.sub.3    H   CH.sub.3                OCH.sub.3                        5-Cl    OCH.sub.3    H   CH.sub.3                CH.sub.3                        6-Cl    OCH.sub.3    H   CH.sub.3                OCH.sub.3                        6-Cl    OCH.sub.3    CH.sub.3        CH.sub.3                CH.sub.3                        4-Cl    OCH.sub.3    H   CH.sub.3                CH.sub.3                        4-Br    OCH.sub.3    H   CH.sub.3                CH.sub.3                        5-Br    OCH.sub.3    H   CH.sub.3                CH.sub.3                        6-Br    OCH.sub.3    H   CH.sub.3                CH.sub.3                        4-F     OCH.sub.3    H   CH.sub.3                CH.sub.3                        5-F     OCH.sub.3    H   CH.sub.3                CH.sub.3                        6-F     OCH.sub.3    H   CH.sub.3                CH.sub.3                        4-CH.sub.3                                OCH.sub.3    H   CH.sub.3                CH.sub.3                        5-CH.sub.3                                OCH.sub.3    H   CH.sub.3                CH.sub.3                        6-CH.sub.3                                OCH.sub.3    H   CH.sub.3                CH.sub.3                        6-CH.sub.3                                CH.sub.3    H   CH.sub.3                CH.sub.3                        4-OCH.sub.3                                OCH.sub.3    H   CH.sub.3                CH.sub.3                        5-OCH.sub.3                                OCH.sub.3    H   CH.sub.3                CH.sub.3                        6-OCH.sub.3                                OCH.sub.3    H   CH.sub.3                CH.sub.3                        6-OCH.sub.3                                CH.sub.3    H   CH.sub.3                CH.sub.3                        4-SCH.sub.3                                OCH.sub.3    H   CH.sub.3                CH.sub.3                        5-SCH.sub.3                                OCH.sub.3    H   CH.sub.3                CH.sub.3                        6-SCH.sub.3                                OCH.sub.3    H   CH.sub.3                CH.sub.3                        4-SCH.sub.2 CH.sub.3                                OCH.sub.3    H   CH.sub.3                CH.sub.3                        5-SCH.sub.2 CH.sub.3                                OCH.sub.3    H   CH.sub.3                CH.sub.3                        6-SCH.sub.2 CH.sub.3                                OCH.sub.3    H   CH.sub.3                CH.sub.3                        4-N(CH.sub.3).sub.2                                OCH.sub.3    H   CH.sub.3                CH.sub.3                        5-N(CH.sub.3).sub.2                                OCH.sub.3    H   CH.sub.3                CH.sub.3                        6-N(CH.sub.3).sub.2                                OCH.sub.3    H   CH.sub.3                CH.sub.3                        4-SCF.sub.2 H                                OCH.sub.3    H   CH.sub.3                CH.sub.3                        5-SCF.sub.2 H                                OCH.sub.3    H   CH.sub.3                CH.sub.3                        6-SCF.sub.2 H                                OCH.sub.3    H   CH.sub.3                CH.sub.3                        4-CF.sub.3                                OCH.sub.3    H   CH.sub.3                CH.sub.3                        5-CF.sub.3                                OCH.sub.3    H   CH.sub.3                CH.sub.3                        6-CF.sub.3                                OCH.sub.3    H   CH.sub.3                CH.sub.3                        4-OCF.sub.2 H                                OCH.sub.3    H   CH.sub.3                CH.sub.3                        5-OCH.sub.2 H                                OCH.sub.3    H   CH.sub.3                CH.sub.3                        6-OCF.sub.2 H                                OCH.sub.3    H   (CH.sub.2).sub.2                        H       OCH.sub.3    H   (CH.sub.2).sub.3                        H       OCH.sub.3    H   (CH.sub.2).sub.4                        H       OCH.sub.3    __________________________________________________________________________

                                      TABLE 3    __________________________________________________________________________     ##STR18##    R   R.sub.1               R.sub.2                      R.sub.3 X     m.p. (°C.)    __________________________________________________________________________    H   H      CH.sub.3                      H       OCH.sub.3    H   H      CH.sub.2 CH.sub.3                      H       OCH.sub.3    H   H      CH.sub.2 CH.sub.2 CH.sub.3                      H       OCH.sub.3    H   H      CH(CH.sub.3).sub.2                      H       OCH.sub.3    H   H      OCH.sub.3                      H       OCH.sub.3    H   H      OCH.sub.2 CH.sub.3                      H       OCH.sub.3    H   H      CH.sub.3                      H       CH.sub.3    H   H      CH.sub.2 CH.sub.3                      H       CH.sub.3    H   H      CH.sub.2 CH.sub.2 CH.sub.3                      H       CH.sub.3    H   H      CH(CH.sub.3).sub.2                      H       CH.sub.3    H   H      OCH.sub.3                      H       CH.sub.3    H   H      OCH.sub.2 CH.sub.3                      H       CH.sub.3    H   H      CH.sub.3                      H       Cl    H   H      CH.sub.2 CH.sub.3                      H       Cl    H   H      CH.sub.2 CH.sub.2 CH.sub.3                      H       Cl    H   H      CH(CH.sub.3).sub.2                      H       Cl    H   H      OCH.sub.3                      H       Cl    H   H      OCH.sub.2 CH.sub.3                      H       Cl    H   H      CH.sub.3                      H       CH.sub.2 F    H   H      CH.sub.2 CH.sub.3                      H       CH.sub.2 F    H   H      OCH.sub.3                      H       CH.sub.2 F    H   H      CH.sub.3                      H       OCH.sub.2 CH.sub.3    H   H      CH.sub.2 CH.sub.3                      H       OCH.sub.2 CH.sub.3    H   H      OCH.sub.3                      H       OCH.sub.2 CH.sub.3    H   H      CH.sub.3                      H       CH.sub.2 OCH.sub.3    H   H      CH.sub.2 CH.sub.3                      H       CH.sub.2 OCH.sub.3    H   H      OCH.sub.3                      H       CH.sub.2 OCH.sub.3    CH.sub.3        H      CH.sub.3                      H       OCH.sub.3    CH.sub.3        H      OCH.sub.3                      H       OCH.sub.3    CH.sub.3        H      CH.sub.3                      H       CH.sub.3    CH.sub.3        H      OCH.sub.3                      H       CH.sub.3    CH.sub.3        H      CH.sub.3                      H       Cl    CH.sub.3        H      OCH.sub.3                      H       Cl    CH.sub.3        H      CH.sub.3                      H       CH.sub.2 F    CH.sub.3        H      CH.sub.3                      H       CH.sub. 2 OCH.sub.3    H   CH.sub.3               CH.sub.3                      H       OCH.sub.3                                    202-204 d    H   CH.sub.3               CH.sub.2 CH.sub.3                      H       OCH.sub.3    H   CH.sub.3               CH.sub.2 CH.sub.2 CH.sub.3                      H       OCH.sub.3    H   CH.sub.3               CH(CH.sub.3).sub.2                      H       OCH.sub.3    H   CH.sub.3               OCH.sub.3                      H       OCH.sub.3    H   CH.sub.3               OCH.sub.2 CH.sub.3                      H       OCH.sub.3    H   CH.sub.3               CH.sub.3                      H       CH.sub.3    H   CH.sub.3               CH.sub.2 CH.sub.3                      H       CH.sub.3    H   CH.sub.3               CH.sub.2 CH.sub.2 CH.sub.3                      H       CH.sub.3    H   CH.sub.3               CH(CH.sub.3).sub.2                      H       CH.sub.3    H   CH.sub.3               OCH.sub.3                      H       CH.sub.3    H   CH.sub.3               OCH.sub.2 CH.sub.3                      H       CH.sub.3    H   CH.sub.3               CH.sub.3                      H       Cl    H   CH.sub.3               CH.sub.2 CH.sub.3                      H       Cl    H   CH.sub.3               CH.sub.2 CH.sub.2 CH.sub.3                      H       Cl    H   CH.sub.3               CH(CH.sub.3).sub.2                      H       Cl    H   CH.sub.3               OCH.sub.3                      H       Cl    H   CH.sub.3               OCH.sub.2 CH.sub.3                      H       Cl    H   CH.sub.3               CH.sub.3                      H       CH.sub.2 F    H   CH.sub.3               CH.sub.2 CH.sub.3                      H       CH.sub.2 F    H   CH.sub.3               OCH.sub.3                      H       CH.sub.2 F    H   CH.sub.3               CH.sub.3                      H       OCH.sub.2 CH.sub.3    H   CH.sub.3               CH.sub.2 CH.sub.3                      H       OCH.sub.2 CH.sub.3    H   CH.sub.3               OCH.sub.3                      H       OCH.sub.2 CH.sub.3    H   CH.sub.3               CH.sub.3                      H       CH.sub.2 OCH.sub.3    H   CH.sub.3               CH.sub.2 CH.sub.3                      H       CH.sub.2 OCH.sub.3    H   CH.sub.3               OCH.sub.3                      H       CH.sub.2 OCH.sub.3    CH.sub.3        CH.sub.3               CH.sub.3                      H       OCH.sub.3    CH.sub.3        CH.sub.3               OCH.sub.3                      H       OCH.sub.3    CH.sub.3        CH.sub.3               CH.sub.3                      H       CH.sub.3    CH.sub.3        CH.sub.3               OCH.sub.3                      H       CH.sub.3    CH.sub.3        CH.sub.3               CH.sub.3                      H       Cl    CH.sub.3        CH.sub.3               OCH.sub.3                      H       Cl    CH.sub.3        CH.sub.3               CH.sub.3                      H       CH.sub.2 F    CH.sub.3        CH.sub.3               CH.sub.3                      H       CH.sub.2 OCH.sub.3    H   CH.sub.2 CH.sub.3               CH.sub.2 CH.sub.3                      H       OCH.sub.3    H   CH.sub.2 CH.sub.3               CH.sub.2 CH.sub.2 CH.sub.3                      H       OCH.sub.3    H   CH.sub.2 CH.sub.3               OCH.sub.3                      H       OCH.sub.3    H   CH.sub.2 CH.sub.3               CH.sub.2 CH.sub.3                      H       CH.sub.3    H   CH.sub.2 CH.sub.3               CH.sub.2 CH.sub.2 CH.sub.3                      H       CH.sub.3    H   CH.sub.2 CH.sub.3               OCH.sub.3                      H       CH.sub.3    H   CH.sub.2 CH.sub.3               CH.sub.2 CH.sub.3                      H       Cl    H   CH.sub.2 CH.sub.3               CH.sub.2 CH.sub.2 CH.sub.3                      H       Cl    H   CH.sub.2 CH.sub.3               OCH.sub.3                      H       Cl    H   CH.sub.2 CH.sub.3               CH.sub.2 CH.sub.3                      H       CH.sub.2 F    H   CH.sub.2 CH.sub.3               CH.sub.2 CH.sub.3                      H       OCH.sub.2 CH.sub.3    H   CH.sub.2 CH.sub.3               CH.sub.2 CH.sub.3                      H       CH.sub.2 OCH.sub.3    CH.sub.3        CH.sub.2 CH.sub.3               CH.sub.2 CH.sub.3                      H       OCH.sub.3    CH.sub.3        CH.sub.2 CH.sub.3               CH.sub.2 CH.sub.3                      H       CH.sub.3    CH.sub.3        CH.sub.2 CH.sub.3               CH.sub.2 CH.sub.3                      H       Cl    H   CH.sub.2 CH.sub.2 CH.sub.3               CH.sub.2 CH.sub.2 CH.sub.3                      H       OCH.sub.3    H   CH.sub.2 CH.sub.2 CH.sub.3               OCH.sub.3                      H       OCH.sub.3    H   CH.sub.2 CH.sub.2 CH.sub.3               CH.sub.2 CH.sub.2 CH.sub.3                      H       CH.sub.3    H   CH.sub.2 CH.sub.2 CH.sub.3               OCH.sub.3                      H       CH.sub.3    H   CH.sub.2 CH.sub.2 CH.sub.3               CH.sub.2 CH.sub.2 CH.sub.3                      H       Cl    H   CH.sub.2 CH.sub.2 CH.sub.3               OCH.sub.3                      H       Cl    H   CH(CH.sub.3).sub.2               CH(CH.sub.3).sub.2                      H       OCH.sub.3    H   H      CH.sub.3                      2-Cl    OCH.sub.3    H   H      OCH.sub.3                      2-Cl    OCH.sub.3    H   H      CH.sub.3                      5-Cl    OCH.sub.3    H   H      OCH.sub.3                      5-Cl    OCH.sub.3    H   H      CH.sub.3                      6-Cl    OCH.sub.3    H   H      OCH.sub.3                      6-Cl    OCH.sub.3    CH.sub.3        H      CH.sub.3                      2-Cl    OCH.sub.3    H   CH.sub.3               CH.sub.3                      2-Cl    OCH.sub.3    H   CH.sub.3               OCH.sub.3                      2-Cl    OCH.sub.3    H   CH.sub.3               CH.sub.3                      5-Cl    OCH.sub.3    H   CH.sub.3               OCH.sub.3                      5-Cl    OCH.sub.3    H   CH.sub.3               CH.sub.3                      6-Cl    OCH.sub.3    H   CH.sub.3               OCH.sub.3                      6-Cl    OCH.sub.3    CH.sub.3        CH.sub.3               CH.sub.3                      2-Cl    OCH.sub.3    H   CH.sub.3               CH.sub.3                      2-Br    OCH.sub.3    H   CH.sub.3               CH.sub.3                      5-Br    OCH.sub.3    H   CH.sub.3               CH.sub.3                      6-Br    OCH.sub.3    H   CH.sub.3               CH.sub.3                      2-F     OCH.sub.3    H   CH.sub.3               CH.sub.3                      5-F     OCH.sub.3    H   CH.sub.3               CH.sub.3                      6-F     OCH.sub.3    H   CH.sub.3               CH.sub.3                      2-CH.sub.3                              OCH.sub.3    H   CH.sub.3               CH.sub.3                      5-CH.sub.3                              OCH.sub.3    H   CH.sub.3               CH.sub.3                      6-CH.sub.3                              OCH.sub.3    H   CH.sub.3               CH.sub.3                      6-CH.sub.3                              CH.sub.3    H   CH.sub.3               CH.sub.3                      2-OCH.sub.3                              OCH.sub.3    H   CH.sub.3               CH.sub.3                      5-OCH.sub.3                              OCH.sub.3    H   CH.sub.3               CH.sub.3                      6-OCH.sub.3                              OCH.sub.3    H   CH.sub.3               CH.sub.3                      6-OCH.sub.3                              CH.sub.3    H   CH.sub.3               CH.sub.3                      2-SCH.sub.3                              OCH.sub.3    H   CH.sub.3               CH.sub.3                      5-SCH.sub.3                              OCH.sub.3    H   CH.sub.3               CH.sub.3                      6-SCH.sub.3                              OCH.sub.3    H   CH.sub.3               CH.sub.3                      2-SCH.sub.2 CH.sub.3                              OCH.sub.3    H   CH.sub.3               CH.sub.3                      5-SCH.sub.2 CH.sub.3                              OCH.sub.3    H   CH.sub.3               CH.sub.3                      6-SCH.sub.2 CH.sub.3                              OCH.sub.3    H   CH.sub.3               CH.sub.3                      2-N(CH.sub.3).sub.2                              OCH.sub.3    H   CH.sub.3               CH.sub.3                      5-N(CH.sub.3).sub.2                              OCH.sub.3    H   CH.sub.3               CH.sub.3                      6-N(CH.sub.3).sub.2                              OCH.sub.3    H   CH.sub.3               CH.sub.3                      2-SCF.sub.2 H                              OCH.sub.3    H   CH.sub.3               CH.sub.3                      5-SCF.sub.2 H                              OCH.sub.3    H   CH.sub.3               CH.sub.3                      6-SCF.sub.2 H                              OCH.sub.3    H   CH.sub.3               CH.sub.3                      2-CF.sub.3                              OCH.sub.3    H   CH.sub.3               CH.sub.3                      5-CF.sub.3                              OCH.sub.3    H   CH.sub.3               CH.sub.3                      6-CF.sub.3                              OCH.sub.3    H   CH.sub.3               CH.sub.3                      2-OCF.sub.2 H                              OCH.sub.3    H   CH.sub.3               CH.sub.3                      5-OCF.sub.2 H                              OCH.sub.3    H   CH.sub.3               CH.sub.3                      6-OCF.sub.2 H                              OCH.sub.3    H   (CH.sub.2).sub.2                      H       OCH.sub.3    H   (CH.sub.2).sub.3                      H       OCH.sub.3    H   (CH.sub.2).sub.4                      H       OCH.sub.3    __________________________________________________________________________

                                      TABLE 4    __________________________________________________________________________     ##STR19##    R   R.sub.1               R.sub.2                      R.sub.3                             X     m.p. (°C.)    __________________________________________________________________________    H   H      CH.sub.3                      H      OCH.sub.3    H   H      CH.sub.2 CH.sub.3                      H      OCH.sub.3    H   H      CH.sub.2 CH.sub.2 CH.sub.3                      H      OCH.sub.3    H   H      CH(CH.sub.3).sub.2                      H      OCH.sub.3    H   H      OCH.sub.3                      H      OCH.sub.3    H   H      OCH.sub.2 CH.sub.3                      H      OCH.sub.3    H   H      CH.sub.3                      H      CH.sub.3    H   H      CH.sub.2 CH.sub.3                      H      CH.sub.3    H   H      CH.sub.2 CH.sub.2 CH.sub.3                      H      CH.sub.3    H   H      CH(CH.sub.3).sub.2                      H      CH.sub.3    H   H      OCH.sub.3                      H      CH.sub.3    H   H      OCH.sub.2 CH.sub.3                      H      CH.sub.3    H   H      CH.sub.3                      H      Cl    H   H      CH.sub.2 CH.sub.3                      H      Cl    H   H      CH.sub.2 CH.sub.2 CH.sub.3                      H      Cl    H   H      CH(CH.sub.3).sub.2                      H      Cl    H   H      OCH.sub.3                      H      Cl    H   H      OCH.sub.2 CH.sub.3                      H      Cl    H   H      CH.sub.3                      H      CH.sub.2 F    H   H      CH.sub.2 CH.sub.3                      H      CH.sub.2 F    H   H      OCH.sub.3                      H      CH.sub.2 F    H   H      CH.sub.3                      H      OCH.sub.2 CH.sub.3    H   H      CH.sub.2 CH.sub.3                      H      OCH.sub.2 CH.sub.3    H   H      OCH.sub.3                      H      OCH.sub.2 CH.sub.3    H   H      CH.sub.3                      H      CH.sub.2 OCH.sub.3    H   H      CH.sub.2 CH.sub.3                      H      CH.sub.2 OCH.sub.3    H   H      OCH.sub.3                      H      CH.sub.2 OCH.sub.3    CH.sub.3        H      CH.sub.3                      H      OCH.sub.3    CH.sub.3        H      OCH.sub.3                      H      OCH.sub.3    CH.sub.3        H      CH.sub.3                      H      CH.sub.3    CH.sub.3        H      OCH.sub.3                      H      CH.sub.3    CH.sub.3        H      CH.sub.3                      H      Cl    CH.sub.3        H      OCH.sub.3                      H      Cl    CH.sub.3        H      CH.sub.3                      H      CH.sub.2 F    CH.sub.3        H      CH.sub.3                      H      CH.sub.2 OCH.sub.3    H   CH.sub.3               CH.sub.3                      H      OCH.sub.3    H   CH.sub.3               CH.sub.2 CH.sub.3                      H      OCH.sub.3    H   CH.sub.3               CH.sub.2 CH.sub.2 CH.sub.3                      H      OCH.sub.3    H   CH.sub.3               CH(CH.sub.3).sub.2                      H      OCH.sub.3    H   CH.sub.3               OCH.sub.3                      H      OCH.sub.3    H   CH.sub.3               OCH.sub.2 CH.sub.3                      H      OCH.sub.3    H   CH.sub.3               CH.sub.3                      H      CH.sub.3    H   CH.sub.3               CH.sub.2 CH.sub.3                      H      CH.sub.3    H   CH.sub.3               CH.sub.2 CH.sub.2 CH.sub.3                      H      CH.sub.3    H   CH.sub.3               CH(CH.sub.3).sub.2                      H      CH.sub.3    H   CH.sub.3               OCH.sub.3                      H      CH.sub.3    H   CH.sub.3               OCH.sub.2 CH.sub.3                      H      CH.sub.3    H   CH.sub.3               CH.sub.3                      H      Cl    H   CH.sub.3               CH.sub.2 CH.sub.3                      H      Cl    H   CH.sub.3               CH.sub.2 CH.sub.2 CH.sub.3                      H      Cl    H   CH.sub.3               CH(CH.sub.3).sub.2                      H      Cl    H   CH.sub.3               OCH.sub.3                      H      Cl    H   CH.sub.3               OCH.sub.2 CH.sub.3                      H      Cl    H   CH.sub.3               CH.sub.3                      H      CH.sub.2 F    H   CH.sub.3               CH.sub.2 CH.sub.3                      H      CH.sub.2 F    H   CH.sub.3               OCH.sub.3                      H      CH.sub.2 F    H   CH.sub.3               CH.sub.3                      H      OCH.sub.2 CH.sub.3    H   CH.sub.3               CH.sub.2 CH.sub.3                      H      OCH.sub.2 CH.sub.3    H   CH.sub.3               OCH.sub.3                      H      OCH.sub.2 CH.sub.3    H   CH.sub.3               CH.sub.3                      H      CH.sub.2 OCH.sub.3    H   CH.sub.3               CH.sub.2 CH.sub.3                      H      CH.sub.2 OCH.sub.3    H   CH.sub.3               OCH.sub.3                      H      CH.sub.2 OCH.sub.3    CH.sub.3        CH.sub.3               CH.sub.3                      H      OCH.sub.3    CH.sub.3        CH.sub.3               OCH.sub.3                      H      OCH.sub.3    CH.sub.3        CH.sub.3               CH.sub.3                      H      CH.sub.3    CH.sub.3        CH.sub.3               OCH.sub.3                      H      CH.sub.3    CH.sub.3        CH.sub.3               CH.sub.3                      H      Cl    CH.sub.3        CH.sub.3               OCH.sub.3                      H      Cl    CH.sub.3        CH.sub.3               CH.sub.3                      H      CH.sub.2 F    CH.sub.3        CH.sub.3               CH.sub.3                      H      CH.sub.2 OCH.sub.3    H   CH.sub.2 CH.sub.3               CH.sub.2 CH.sub.3                      H      OCH.sub.3    H   CH.sub.2 CH.sub.3               CH.sub.2 CH.sub.2 CH.sub.3                      H      OCH.sub.3    H   CH.sub.2 CH.sub.3               OCH.sub.3                      H      OCH.sub.3    H   CH.sub.2 CH.sub.3               CH.sub.2 CH.sub.3                      H      CH.sub.3    H   CH.sub.2 CH.sub.3               CH.sub.2 CH.sub.2 CH.sub.3                      H      CH.sub.3    H   CH.sub.2 CH.sub.3               OCH.sub.3                      H      CH.sub.3    H   CH.sub.2 CH.sub.3               CH.sub.2 CH.sub.3                      H      Cl    H   CH.sub.2 CH.sub.3               CH.sub.2 CH.sub.2 CH.sub.3                      H      Cl    H   CH.sub.2 CH.sub.3               OCH.sub.3                      H      Cl    H   CH.sub.2 CH.sub.3               CH.sub.2 CH.sub.3                      H      CH.sub.2 F    H   CH.sub.2 CH.sub.3               CH.sub.2 CH.sub.3                      H      OCH.sub.2 CH.sub.3    H   CH.sub.2 CH.sub.3               CH.sub.2 CH.sub.3                      H      CH.sub.2 OCH.sub.3    CH.sub.3        CH.sub.2 CH.sub.3               CH.sub.2 CH.sub.3                      H      OCH.sub.3    CH.sub.3        CH.sub.2 CH.sub.3               CH.sub.2 CH.sub.3                      H      CH.sub.3    CH.sub.3        CH.sub.2 CH.sub.3               CH.sub.2 CH.sub.3                      H      Cl    H   CH.sub.2 CH.sub.2 CH.sub.3               CH.sub.2 CH.sub.2 CH.sub.3                      H      OCH.sub.3    H   CH.sub.2 CH.sub.2 CH.sub.3               OCH.sub.3                      H      OCH.sub.3    H   CH.sub.2 CH.sub.2 CH.sub.3               CH.sub.2 CH.sub.2 CH.sub.3                      H      CH.sub.3    H   CH.sub.2 CH.sub.2 CH.sub.3               OCH.sub.3                      H      CH.sub.3    H   CH.sub.2 CH.sub.2 CH.sub.3               CH.sub.2 CH.sub.2 CH.sub.3                      H      Cl    H   CH.sub.2 CH.sub.2 CH.sub.3               OCH.sub.3                      H      Cl    H   CH(CH.sub.3).sub.2               CH(CH.sub.3).sub.2                      H      OCH.sub.3    H   H      CH.sub.3                      2-Cl   OCH.sub.3    H   H      OCH.sub.3                      2-Cl   OCH.sub.3    H   H      CH.sub.3                      5-Cl   OCH.sub.3    H   H      OCH.sub.3                      5-Cl   OCH.sub.3    H   H      CH.sub.3                      6-Cl   OCH.sub.3    H   H      OCH.sub.3                      6-Cl   OCH.sub.3    CH.sub.3        H      CH.sub.3                      6-Cl   OCH.sub.3    H   CH.sub.3               CH.sub.3                      2-Cl   OCH.sub.3    H   CH.sub.3               OCH.sub.3                      2-Cl   OCH.sub.3    H   CH.sub.3               CH.sub.3                      5-Cl   OCH.sub.3    H   CH.sub.3               OCH.sub.3                      5-Cl   OCH.sub.3    H   CH.sub.3               CH.sub.3                      6-Cl   OCH.sub.3    H   CH.sub.3               OCH.sub.3                      6-Cl   OCH.sub.3    CH.sub.3        CH.sub.3               CH.sub.3                      6-Cl   OCH.sub.3    H   CH.sub.3               CH.sub.3                      2-Br   OCH.sub.3    H   CH.sub.3               CH.sub.3                      5-Br   OCH.sub.3    H   CH.sub.3               CH.sub.3                      6-Br   OCH.sub.3    H   CH.sub.3               CH.sub.3                      2-F    OCH.sub.3    H   CH.sub.3               CH.sub.3                      5-F    OCH.sub.3    H   CH.sub.3               CH.sub.3                      6-F    OCH.sub.3    H   CH.sub.3               CH.sub.3                      2-CH.sub.3                             OCH.sub.3    H   CH.sub.3               CH.sub.3                      5-CH.sub.3                             OCH.sub.3    H   CH.sub. 3               CH.sub.3                      6-CH.sub.3                             OCH.sub.3    H   CH.sub.3               CH.sub.3                      6-CH.sub.3                             CH.sub.3    H   CH.sub.3               CH.sub.3                      2-OCH.sub.3                             OCH.sub.3    H   CH.sub.3               CH.sub.3                      5-OCH.sub.3                             OCH.sub.3    H   CH.sub.3               CH.sub.3                      6-OCH.sub.3                             OCH.sub.3    H   CH.sub.3               CH.sub.3                      6-OCH.sub.3                             CH.sub.3    H   CH.sub.3               CH.sub.3                      2-SCH.sub.3                             OCH.sub.3    H   CH.sub.3               CH.sub.3                      5-SCH.sub.3                             OCH.sub.3    H   CH.sub.3               CH.sub.3                      6-SCH.sub.3                             OCH.sub.3    H   CH.sub.3               CH.sub.3                      2-SCH.sub.2 CH.sub.3                             OCH.sub.3    H   CH.sub.3               CH.sub.3                      5-SCH.sub.2 CH.sub.3                             OCH.sub.3    H   CH.sub.3               CH.sub.3                      6-SCH.sub.2 CH.sub.3                             OCH.sub.3    H   CH.sub.3               CH.sub.3                      2-N(CH.sub.3).sub.2                             OCH.sub.3    H   CH.sub.3               CH.sub.3                      5-N(CH.sub.3).sub.2                             OCH.sub.3    H   CH.sub.3               CH.sub.3                      6-N(CH.sub.3).sub.2                             OCH.sub.3    H   CH.sub.3               CH.sub.3                      2-SCF.sub.2 H                             OCH.sub.3    H   CH.sub.3               CH.sub.3                      5-SCF.sub.2 H                             OCH.sub.3    H   CH.sub.3               CH.sub.3                      6-SCF.sub.2 H                             OCH.sub.3    H   CH.sub.3               CH.sub.3                      2-CF.sub.3                             OCH.sub.3    H   CH.sub.3               CH.sub.3                      5-CF.sub.3                             OCH.sub.3    H   CH.sub.3               CH.sub.3                      6-CF.sub.3                             OCH.sub.3    H   CH.sub.3               CH.sub.3                      2-OCF.sub.2 H                             OCH.sub.3    H   CH.sub.3               CH.sub.3                      5-OCF.sub.2 H                             OCH.sub.3    H   CH.sub.3               CH.sub.3                      6-OCF.sub.2 H                             OCH.sub.3    H   (CH.sub.2).sub.2                      H      OCH.sub.3    H   (CH.sub.2).sub.3                      H      OCH.sub.3    H   (CH.sub.2).sub.4                      H      OCH.sub.3    __________________________________________________________________________

Formulations

Useful formulations of the compounds of Formula I can be prepared inconventional ways. They include dusts, granules, pellets, solutions,suspensions emulsions, wettable powders, emulsifiable concentrates andthe like. Many of these may be applied directly. Sprayable formulationscan be extended in suitable media and used at spray volumes of from afew liters to several hundred liters per hectare. High strengthcompositions are primarily used as intermediates for furtherformulation. The formulations, broadly, contain about 0.1% to 99% byweight of active ingredient(s) and at least one of (a) about 0.1% to 20%surfactant(s) and (b) about 1% to 99.9% solid or liquid diluent(s). Morespecifically, they will contain these ingredients in the followingapproximate proportions:

    ______________________________________                Active  Weight Percent*                Ingredient                        Diluent(s)                                  Surfactant(s)    ______________________________________    Wettable Powders                  20-90      0-74     1-10    Oil Suspensions,                   3-50     40-95     0-15    Emulsions, Solutions,    (including Emulsifiable    Concentrates)    Aqueous Suspension                  10-50     40-84     1-20    Dusts          1-25     70-99     0-5    Granules and Pellets                  0.1-95      5-99.9  0-15    High Strength 90-99      0-10     0-2    Compositions    ______________________________________     *Active ingredient plus at least one of a Surfactant or a Diluent equals     100 weight percent.

Lower or higher levels of active ingredient can, of course, be presentdepending on the intended use and the physical properties of thecompound. Higher ratios of surfactant to active ingredient are sometimesdesirable, and are achieved by incorporation into the formulation or bytank mixing.

Typical solid diluents are described in Watkins, et al., "Handbook ofInsecticide Dust Diluents and Carriers", 2nd Ed., Dorland Books,Caldwell, N.J., but other solids, either mined or manufactured, may beused. The more absorptive diluents are preferred for wettable powdersand the denser ones for dusts. Typical liquid diluents and solvents aredescribed in Marsden, "Solvents Guide," 2nd Ed., Interscience, New York,1950. Solubility under 0.1% is preferred for suspension concentrates;solution concentrates are preferably stable against phase separation at0° C. "McCutcheon's Detergents and Emulsifiers Annual", MC PublishingCorp., Ridgewood, N.J., as well as Sisely and Wood, "Encyclopedia ofSurface Active Agents", Chemical Publishing Co., Inc., New York, 1964,list surfactants and recommended uses. All formulations can containminor amounts of additives to reduce foaming, caking, corrosion,microbiological growth, and the like.

The methods of making such compositions are well known. Solutions areprepared by simply mixing the ingredients. Fine solid compositions aremade by blending and, usually, grinding as in a hammer or fluid energymill. Suspensions are prepared by wet milling (see, for example,Littler, U.S. Pat. No. 3,060,084). Granules and pellets may be made byspraying the active material upon preformed granular carriers or byagglomeration techniques. See Browning, "Agglomeration", ChemicalEngineering, Dec. 4, 1967, pp. 147ff. and "Perry's Chemical Engineer'sHandbook", 5th Ed., McGraw-Hill, New York, 1973, pages 8 to 57 andfollowing.

For further information regarding the art of formulation, see forexample: U.S. Pat. No. 3,235,361, column 6, line 16 through column 7,line 19 and Examples 10 through 41; U.S. Pat. No. 3,309,192, column 5,line 43 through column 7, line 62 and Examples 8, 12, 15, 39, 41, 52,53, 58, 132, 138 to 140, 162 to 164, 166, 167 and 169 to 182; U.S. Pat.No. 2,891,855, column 3, line 66 through column 5, line 17 and Examples1 to 4; Klingman, "Weed Control as a Science", John Wiley and Sons,Inc., New York, 1961, pages 81 to 96; and Fryer et al., "Weed ControlHandbook", 5th Ed., Blackwell Scientific Publications, Oxford, 1968,pages 101 to 103.

In the following Examples, all parts are by weight unless otherwiseindicated.

EXAMPLE 13

    ______________________________________    Wettable Powder    ______________________________________    2-[[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]amino-                                 50%    sulfonyl]-N,N-dimethyl-3-pyridinecarboxamide    sodium alkylnaphthalenesulfonate                                 2%    low viscosity methyl cellulose                                 2%    diatomaceous earth           46%    ______________________________________

The ingredients are blended, coarsely hammer-milled and then air-milledto produce particles essentially all below 10 microns in diameter. Theproduct is reblended before packaging.

EXAMPLE 14

    ______________________________________    Granule    ______________________________________    Wettable Powder of Example 13                               5%    attapulgite granules       95%    (U.S.S. 20 to 40 mesh; 0.84 to 0.42 mm)    ______________________________________

A slurry of wettable powder containing 25% solids is sprayed on thesurface of attapulgite granules in a double-cone blender. The granulesare dried and packaged.

EXAMPLE 15

    ______________________________________    Extruded Pellet    ______________________________________    2-[[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]amino-                                 25%    sulfonyl]-N,N-dimethyl-3-pyridinecarboxamide    anhydrous sodium sulfate     10%    crude calcium ligninsulfonate                                 5%    sodium alkylnaphthalenesulfonate                                 1%    calcium/magnesium bentonite  59%    ______________________________________

The ingredients are blended, hammer-milled and then moistened with about12% water. The mixture is extruded as cylinders about 3 mm diameterwhich are cut to produce pellets about 3 mm long. These may be useddirectly after drying, or the dried pellets may be crushed to pass aU.S.S. No. 20 sieve (0.84 mm openings). The granules held on a U.S.S.No. 40 sieve (0.42 mm openings) may be packaged for use and the finesrecycled.

EXAMPLE 16

    ______________________________________    Low Strength Granule    ______________________________________    2-[[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]amino-                                 1%    sulfonyl]-N,N-dimethyl-3-pyridinecarboxamide    N,N-dimethylformamide        9%    attapulgite granules         90%    (U.S.S. 20 to 40 sieve)    ______________________________________

The active ingredient is dissolved in the solvent and the solution issprayed upon dedusted granules in a double cone blender. After sprayingof the solution has been completed, the blender is allowed to run for ashort period and then the granules are packaged.

EXAMPLE 17

    ______________________________________    Aqueous Suspension    ______________________________________    2-[[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]amino-                                 40%    sulfonyl]-N,N-dimethyl-3-pyridinecarboxamide    polyacrylic acid thickener   0.3%    dodecylphenol polyethylene glycol ether                                 0.5%    disodium phosphate           1%    monosodium phosphate         0.5%    polyvinyl alcohol            1.0%    water                        56.7%    ______________________________________

The ingredients are blended and ground together in a sand mill toproduce particles essentially all under 5 microns in size.

EXAMPLE 18

    ______________________________________    Oil Suspension    ______________________________________    2-[[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]amino-                                 35%    sulfonyl]-N,N-dimethyl-3-pyridinecarboxamide    blend of polyalcohol carboxylic                                 6%    esters and oil soluble petroleum    sulfonates    xylene                       59%    ______________________________________

The ingredients are combined and ground together in a sand mill toproduce particles essentially all below 5 microns. The product can beused directly, extended with oils, or emulsified in water.

EXAMPLE 19

    ______________________________________    Granule    ______________________________________    2-[[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]amino-                                 80%    sulfonyl]-N,N-dimethyl-3-pyridinecarboxamide    wetting agent                1%    crude ligninsulfonate salt (containing                                 10%    5 to 20% of the natural sugars)    attapulgite clay             9%    ______________________________________

The ingredients are blended and milled to pass through a 100 meshscreen. This material is then added to a fluid bed granulator, the airflow is adjusted to gently fluidize the material, and a fine spray ofwater is sprayed onto the fluidized material. The fluidization andspraying are continued until granules of the desired size range aremade. The spraying is stopped, but fluidization is continued, optionallywith heat, until the water content is reduced to the desired level,generally less than 1%. The material is then discharged, screened to thedesired size range, generally 14 to 100 mesh (1410 to 149 microns), andpackaged for use.

EXAMPLE 20

    ______________________________________    High Strength Concentrate    ______________________________________    2-[[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]amino-                                 99%    sulfonyl]-N,N-dimethyl-3-pyridinecarboxamide    silica aerogel               0.5%    synthetic amorphous silica   0.5%    ______________________________________

The ingredients are blended and ground in a hammer-mill to produce amaterial essentially all passing a U.S.S. No. 50 screen (0.3 mmopening). The concentrate may be formulated further if necessary.

EXAMPLE 21

    ______________________________________    Wettable Powder    ______________________________________    2-[[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]amino-                                 90%    sulfonyl]-N,N-dimethyl-3-pyridinecarboxamide    dioctyl sodium sulfosuccinate                                 0.1%    synthetic fine silica        9.9%    ______________________________________

The ingredients are blended and ground in a hammer-mill to produceparticles essentially all below 100 microns. The material is siftedthrough a U.S.S. No. 50 screen and then packaged.

EXAMPLE 22

    ______________________________________    Wettable Powder    ______________________________________    2-[[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]amino-                                20%    sulfonyl]-N,N-dimethyl-3-pyridinecarboxamide    sodium ligninsulfonate      20%    montmorillonite clay        60%    ______________________________________

The ingredients are thoroughly blended, coarsely hammer-milled and thenair-milled to produce particles essentially all below 10 microns insize. The material is reblended and then packaged.

EXAMPLE 23

    ______________________________________    Dust    ______________________________________    2-[[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]amino-                                10%    sulfonyl]-N,N-dimethyl-3-pyridinecarboxamide    attapulgite                 10%    Pyrophyllite                80%    ______________________________________

The active ingredient is blended with attapulgite and then passedthrough a hammer-mill to produce particles substantially all below 200microns. The ground concentrate is then blended with powderedpyrophyllite until homogeneous.

Utility

Corn (maize) is a very important cereal crop, providing animal feed aswell as food for human consumption. As with all crops, high yieldsdepend on good control of unwanted plants to minimize competitiveeffects on the crop. Since corn is a grass, it is particularly difficultto control other grasses competing with the crop. Many of the compoundsof this invention control weeds in corn both pre- and postemergencewithout significant crop damage. Such compounds are particularly usefulto control such problem weeds as the foxtail (Setaria spp.), fallpanicum (Panicum dichotomiflorum), barnyardgrass (Echinochloacrusgallis), seedling johnsongrass (Sorghum halepense) and shattercane(Sorghum bicolor). They can be used preemergence or postemergence andare most effective when applied postemergence to young weeds. They arealso effective on certain broadleaf weeds such as lambsquarter(Chenopodium album), pigweed (Amaranthus spp.) and jimsonweed (Daturastramonium). The rate used can vary from about 0.5 g/ha to 1000 g/hadepending on the number and age of weeds present, soil type, climate,formulation used and method of application. One of ordinary skill in theart can readily select the exact rate and method of application thatwill provide the desired herbicidal efficacy.

The compounds of this invention may be used in combination with othercommercial herbicides. They are particularly useful in combination withthe following herbicides.

    ______________________________________               Chemical Name    ______________________________________    Common Name    alachlor    2-chloro-2',6'-diethyl-N-(methoxymethyl)-                acetanilide    atrazine    2-chloro-4-(ethylamino)-6-(isopropyl-                amino)-s-triazine    butylate    S-ethyl-diisobutylthiocarbamate    cyanazine   2-[[4-chloro-6-(ethylamino)-s-triazin-2-                yl]amino]-2-methylpropionitrile    dicamba     3,6-dichloro-o-anisic acid    EPTC        S-ethyl dipropylthiocarbamate    linuron     3-(3,4-dichlorophenyl)-1-methoxy-1-                methylurea    metolachlor 2-chloro-N-(2-ethyl-6-methylphenyl)-N-                (2-methoxy-1-methylethyl)acetamide    metribuzin  4-amino-6-tert-butyl-3-(methylthio)-as-                triazine-5(4H)-one    tridiphane  2-(3,5-dichlorophenyl)-2-(2,2,2-tri-                chloroethyl)oxirane    2,4-D       (2,4-dichlorophenoxy)acetic acid    bromoxynil  3,5-dibromo-4-hydroxyphenylcyanide    paraquat    1,1'-dimethyl-4,4-bipyridinium ion    glyphosate  N-(phosphonomethyl)glycine    ______________________________________    Trade Name    Harmony ™                3-[[(4-methoxy-6-methyl-1,3,5-triazin-                2-yl)aminocarbonyl]aminosulfonyl]-2-                thiophenecarboxylic acid, methyl ester    Cinch ® 1-methyl-4-(1-methylethyl)-2-exo-[(2-                methylphenyl)-methoxy]-7-oxabicyclo-                [2.2.1]heptane    --          2-ethoxy-N-[[4-(2,2,2-trifluoroethoxy)-                6-methoxy-1,3,5-triazin-2-yl]amino-                carbonyl]benzenesulfonamide    ______________________________________

The utility of these chemicals is demonstrated in terms of thegreenhouse test data summarized hereafter. The results demonstrate theherbicidal efficacy and corn selectivity of the compounds of thisinvention.

    ______________________________________    Compounds    Compound            R.sub.1    R.sub.2   R.sub.3  X    ______________________________________     ##STR20##    1       CH.sub.3   OCH.sub.3 H        OCH.sub.3    2       CH.sub.3   OCH.sub.3 H        CH.sub.3    3       CH.sub.3   CH.sub.3  6-CH.sub.3                                          OCH.sub.3    4       CH.sub.3   CH.sub.3  6-CH.sub.3                                          CH.sub.3    5       H          CH.sub.3  H        Cl    6       CH.sub.3   CH.sub.2 CH.sub.3                                 H        OCH.sub.3    7       CH.sub.3   CH.sub.2 CH.sub.3                                 H        CH.sub.3    8       CH(CH.sub.3).sub.2                       CH(CH.sub.3).sub.2                                 H        OCH.sub.3    9       CH(CH.sub.3).sub.2                       CH(CH.sub.3).sub.2                                 H        CH.sub.3    10      CH.sub.2 CH.sub.3                       CH.sub.2 CH.sub.3                                 H        OCH.sub.3    11      CH.sub.3   CH.sub.3  H        CH.sub.3    12      CH.sub.3   CH.sub.3  H        OCH.sub.3    13      CH.sub.3   CH.sub.3  H        Cl    14      CH.sub.2 CH.sub.3                       CH.sub.2 CH.sub.3                                 H        Cl    15      CH.sub.3   OCH.sub.3 H        Cl    16      CH.sub.3   CH.sub.3  6-Cl     Cl    17      CH.sub.3   CH.sub.3  6-Cl     OCH.sub.3    18      (CH.sub.2).sub.4 H          OCH.sub.3    19      (CH.sub.2).sub.4 H          Cl    20      (CH.sub.2).sub.4 H          CH.sub.3    21      (CH.sub.2).sub.3 H          OCH.sub.3    22      (CH.sub.2).sub.3 H          CH.sub.3    23      (CH.sub.2).sub.3 H          Cl    24      CH.sub.3   CH.sub.3  6-SCH.sub.3                                          OCH.sub.3    25      CH.sub.3   CH.sub.3  6-SCH.sub.3                                          Cl    26      CH.sub.3   CH.sub.3  6-SCH.sub.3                                          CH.sub.3    27      CH.sub.3   CH.sub.3  6-N(CH.sub.3).sub.2                                          OCH.sub.3    28      CH.sub.3   CH.sub.3  6-SCH.sub.2 CH.sub.3                                          OCH.sub.3    29      CH.sub.3   CH.sub.3  6-SCH.sub.2 CH.sub.3                                          Cl    30      CH.sub.3   CH.sub.3  6-SCH.sub.2 CH.sub.3                                          CH.sub.3    31      H          CH.sub.2 CH.sub.3                                 H        OCH.sub.3    32      H          CH.sub.3  H        OCH.sub.3    33      H          CH.sub.3  H        CH.sub.3     ##STR21##    34      CH.sub.3   CH.sub.3  H        OCH.sub.3     ##STR22##    35      CH.sub.3   CH.sub.3  H        OCH.sub.3    36      CH.sub.3   CH.sub.3  H        Cl    ______________________________________

Test A

Seeds of crabgrass (Digitaria sp.), barnyardgrass (Echinochloacrusgalli), giant foxtail (Setaria faberi), wild oats (Avena fatua),cheatgrass (Bromus secalinus), velvetleaf (Abutilon theophrasti),morningglory (Ipomoea spp.), cocklebur (Xanthium pensylvanicum),sorghum, corn, soybean, sugarbeet, cotton, rice, wheat, barley andpurple nutsedge (Cyperus rotundus) tubers were planted and treatedpreemergence with the test chemicals dissolved in a non-phytotoxicsolvent. At the same time, these crop and weed species were treated witha soil/foliage application. At the time of treatment, the plants rangedin height from 2 to 18 cm. Treated plants and controls were maintainedin a greenhouse for sixteen days, after which all species were comparedto controls and visually rated for response to treatment. The ratings,summarized in Table A, are based on a numerical scale extending from 0=no injury, to 10=complete kill. The accompanying descriptive symbolshave the following meanings:

C=chlorosis/necrosis;

B=burn;

D=defoliation;

E=emergence inhibition;

G=growth retardation;

H=formative effect;

U=unusual pigmentation;

X=axillary stimulation;

S=albinism; and

6Y=abscised buds or flowers.

    TABLE A       CMPD 1 CMPD 2 CMPD 3 CMPD 4 CMPD 5 CMPD 6 CMPD 7 CMPD 8 CMPD 9 CMPD 10 R     ATE = KG/HA 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01     0.050.01 0.05 0.05 0.05 0.4 0.05 0.4       POSTEMERGENCE COTTON 4C,8H 4C,9G 2G 3C,7H 2C,9G 5C,9G 0 3C,8H 0 0     4C,8H 4C,9H 0 2G 1C 3C,5G 4C,9H 4C,8H 4C,9H MORNING GLORY 4C,9H 9C 3C,5H     4C,9G 4C,9G 10C 1H 3C,7H 0 0 3C,8H 4C,9G 3C,5H 4C,9H 2H 4C,8H 4C,9G     4C,9G 10C COCKLEBUR 4G 10C 2C,2H 4C,8H 4C,9H 10C 1H 3C,7H 0 0 4C,9H     5C,9G 3C,5G 4C,9H 3C,7H 4C,9H 4C,9G 4C,9H 10C NUTSEDGE 4C,8G 8G 0 3C,8G     4C,9G 5C,9G 0 2C,8G 0 0 3C,7G 8G 0 2C,5G 3G 2G 3C,7G 4C,9G 6C,9G     CRABGRASS 2G 3C,7G 0 3C,5G 0 8G 0 0 0 0 3G 5G 0 2G 0 0 0 0 3C,7G     BARNYARD GRASS 5C,9H 9C 4C,8H 9C 10C 9C 0 3C,8G 009C9C 2C,5H 5C,9H 9H     3C,8H 9C 9C 9C WILD OATS 5C,9G 6C,9G 4C,9G 5C,9G 3C,6G 5C,9G 0 2C,7G 0 0     3C,7G 4C,9G 2C,8G 4C,9G 0 2C,5G 4C,8G 3C,6G 9C WHEAT 3C,9G 6C,9G 9G 9C     9C 5C,9G 2G 3C,9G 0 0 9G 4C,9G 9G 9G 0 4C,9G 9C 3C,9G 9C CORN 0 0 0 0 0     0 0 0 0 0 0 0 0 0 3C,5H 0 2G 2C,6G 3C,9H SOYBEAN 3C,8G 4C,9G 3H 4C,9G     4C,9G 9C 0 2C,6G 0 0 4C,8G 4C,9G 2G 3C,8G 3C,5H 3G 4C,9H 3C,8G 4C,9G     RICE 9C 9C 4C,9G 9C 9C 9C 2C,5G 9C 0 0 9C 9C 5G 5C,9G 2C,9G 9C 9C 10C 9C     SORGHUM 4C,9G 5C,9G 4C,9H 4C,9G 10C 10C 2C,6G 3C,8H 0 0 10C 10C 2G 4C,9G     2C,9G 4C,9G 9C 10C 10C CHEATGRASS 2C,9G 5C,9G 3C,9G 3C,9G 4C,9G 9C 0     2C,8G 0 0 9C 9C 7G 4C,9G 5G 2C,8G 9C 9C 10C SUGAR BEETS 4C,9G 9C 3C,5H     4C,9H 4C,8H 10C 0 3C,6H 0 0 5C,9H 10C 3C,3H 4C,8H 3C,7G 3C,7H 9C 10C 10C     VELVETLEAF 4C,8H 4C,9H 3C,5G 4C,8H 3C,7H 9C 0 2C,4G 0 0 4C,8H 4C,9H     3C,3H 3C,7H 7G 4C,8H 10C 9C 10C GIANT FOXTAIL 5C,9G 9C 4C,9G 5C,9G 5C,9G     9C 1H 3C,8G 0 -- 4C,9H 9C 2H 4C,9G 2C,5G 3C,7G 6C,9H 4C,9H 9C BARLEY     3C,9G 5C,9G 3C,8G 3C,9G 5C,9G 6C,9G 1C 3C,6G 0 0 4C,9G 4C,9G 3C,7G 4C,9H     3C,5G 3C,9G 9C 4C,9G 9C DOWNY BROME PREEMERGENCE COTTON 2G 8G 0 0 0 7H 0     0 0 0 0 2C,4G 0 0 0 0 2G 3G 4C,8G MORNING GLORY 1H 3H 1C 3G 0 8H 0 2G 0     0 0 3C,7H 0 0 0 0 6H 4G 8G COCKLEBUR -- 6H 0 0 1H -- 0 0 0 -- 0 3C,3H 0     0 -- 0 6H 0 8H NUTSEDGE 3C,5G 9G 0 3G 0 9G 0 0 0 0 0 9G 0 0 0 0 0 0 10E     CRABGRASS 0 3G 0 0 0 2C,2G 0 0 -- 0 0 3G 0 0 0 0 3G 0 2C BARNYARD GRASS     2C 3C,9H 0 0 5G 9H 0 0 0 0 2G 9H 0 0 0 0 0 3C,7H 9C WILD OATS 3G 3C,7G 0     0 0 2C,6G 0 0 0 0 3G 3C,7G 0 0 0 0 0 0 9G WHEAT 3G 2C,8G 0 0 2G 8G 0 0 0     0 5G 3C,9H 0 0 0 0 2C,7G 3G 9G CORN 0 0 0 0 0 0 0 0 0 0 2G 0 0 0 0 0 2G     0 2C,7G SOYBEAN 0 1H 0 0 2G 3C,6H 0 0 0 0 2G 2C,6H 0 0 0 0 0 0 2C,4G     RICE 2C,5G 9H 0 0 7G 9H 0 0 0 0 3C,8H 5C,9H 0 0 0 0 9H 10H 10E SORGHUM     3C,8G 3C,9H 0 0 3C,6G 9H 0 0 0 0 3C,9H 4C,9H 0 0 2C,2G 2C 4C,9G 4C,9H 9C     CHEATGRASS 6G 2C,8G 0 0 0 8G 0 0 0 0 7G 9G 0 0 0 0 2G 5G 10E SUGAR BEETS     3H 3C,8G 0 0 3G 4C,9G 0 0 0 0 3C,8H 4C,9G 0 2H 0 0 2H 3C,5H 10E VELVETLEA     F 3C,3G 7H 1C 3G 0 7H 0 0 0 0 0 3C,3H 0 0 0 0 2G 0 7H GIANT FOXTAIL 2G     3C,8H 0 2G 0 3C,7G 0 0 0 0 0 3C,8H 0 0 0 0 0 0 4G BARLEY 0 3C,6G 0 0 0     9G 0 0 0 0 2C,7G 9G 0 0 0 2G 2C,7G 8G 9G DOWNY BROME       CMPD 11 CMPD 12 CMPD 13 CMPD 14 CMPD 15 CMPD 16 CMPD 17 CMPD 18 CMPD     19 CMPD 20 RATE = KG/HA 0.01 0.05 0.01 0.05 0.05 0.05 0.01 0.05 0.01     0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05       POSTEMERGENCE COTTON 0 2C,6G 9H 4C,9H 3C,5H 7G 0 2G 0 2G 9G 4C,9G     3C,8H 3C,9G 0 1H 0 3C,5G MORNING GLORY 2C,5G 4C,9H 9C 10C 3C,7H 3C,9G     2C,3G 3C,8H 0 2C,3G 5C,9G 10C 4C,9H 10C 2C,2G 3C,6H 3C,4G 3C,8H COCKLEBUR      2G 4G 4G 3C,8G 2C,4G 2C,8G 3G 2C,2H 0 1C,1H 4C,9H 9C 4C,9H 9C 1H 2C,3G     2C,2H 3C,8G NUTSEDGE 0 2C,9G 9G 2C,9G 0 2C,7G 0 -- -- -- -- 8G 8G 9G 0     3G 0 3C,5G CRABGRASS 2G 3C,7G 7G 4C,9G 2C,5G 0 0 3G 0 0 3C,8G 9G 4C,8G     5C,9G 0 2C 0 3C,5G BARNYARD GRASS 2C,5G 4C,8H 4C,9G 9C 3C,8H 3C,9H 2C,3G     3C,9H 0 3C,5G 9C 9C 4C,9G 10C 0 3C,3G 3C,4G 4C,9G WILD OATS 0 5C,9G     3C,9G 3C,9G 2C,3G 0 0 2C,3G 0 0 9G 9G 9G 3C,9G 0 3G 2C,5G 3C,7G WHEAT 7G     9G 8G 3C,9G 4G 0 3G 5G 0 0 2C,9G 4C,9G 4C,9G 9G 0 3G 7G 9G CORN 0 0 0 2G     0 1H 0 0 0 0 0 0 2G 2C,7H 0 0 2G 2C,2G SOYBEAN 0 1H 4H 4C,8H 0 0 0 2G 0     2C,2G 4C,9G 5C,9G 0 1C,1H 0 0 0 3C,5G RICE 2C,8G 5C,9G 5C,9G 5C,9G 3C,9G     3C,6G 0 7G 0 0 5C,9G 5C,9G 3C,9G 5C,9G 0 2G 3C,7G 5C,9G SORGHUM 2C,5G     4C,9G 5C,9G 9C 4C,9G 2C,9G 2C 3C,6G 0 2C,3G 3C,9G 5C,9G 3C,9G 4C,9G 0     2C,2G 0 2C,4G CHEATGRASS 8G 5C,9G 4C,9G 4C,9G 8G 6G 0 5G 0 0 2C,9G 5C,9G     9G 4C,9G 0 2C,8G 9G 5C,9G SUGAR BEETS 1H 3C,6G 5C,9G 5C,9G 3C,7G 4C,8G 0     3C,6G 0 3C,5H 9C 9C 10C 10C 1C 2C,5G 3C,5G 9C VELVETLEAF 0 3C,7H 3C,7H     9C 2G 2G 0 2C 0 1C,1H 3C,6H 3C,8H 4C,9H 4C,9G 0 2C 2C 3C,7H GIANT     FOXTAIL 2C,6G 4C,9G 5C,9G 9C 3C,8G 3G 2G 3C,8G 0 2G 4C,9G 9C 4C,9G 6C,9G     0 2C,2G 3C,5G 4C,9G BARLEY 7G 4C,9G 4C,9G 5C,9G 2C,8G 0 0 7G 0 0 4C,9G     5C,9G 3C,8G 3C,8G 0 1C 2C,7G 9G DOWNY BROME PREEMERGENCE COTTON 0 0 5G     8H 0 2G 0 0 0 0 3G 4C,9G 0 2C,7G 0 0 0 0 MORNING GLORY 0 6G 5H 9G 0 0 0     0 0 0 9G 9G 1C 2C,8H 0 2C,2H 0 0 COCKLEBUR 0 1H 3G -- -- 7H 0 0 0 0 7G     7H 0 3C,7G 0 4G 0 0 NUTSEDGE 0 0 8G 10E 0 0 0 0 0 0 10E 10E 0 9G 0 0 0 0     CRABGRASS 0 2G 2G 3G 0 0 0 0 0 0 0 3C,8G 0 3C,8H 0 0 0 0 BARNYARD GRASS     0 2G 7G 9H 2G 0 0 0 0 0 3C,7G 9H 2G 6G 0 2C 0 0 WILD OATS 0 0 2C,3G     3C,8H 0 0 0 0 0 0 3C,4G 3C,7H 0 1C,2G 0 0 0 0 WHEAT 0 0 8G 9H 0 0 0 0 0     0 9H 2C,9H 4G 9H 0 0 0 0 CORN 0 0 0 4G 0 0 0 2G 0 0 0 3G 0 3C,7H 0 0 0 0     SOYBEAN 0 0 0 3G 0 0 0 3G 0 0 2C,3G 3C,7H 0 1C,3G 0 0 0 1C RICE 0 0 9H     10E 2G 7H 0 2G 0 0 9H 10E 0 2C,6G 0 0 0 0 SORGHUM 0 0 3C,9H 5C,9H 2G     2C,7G 0 0 0 0 3C,9H 9H 0 3C,8H 0 0 0 0 CHEATGRASS 0 0 5G 9H 3G 0 0 0 0 0     0 8H 0 5G 0 3G 0 0 SUGAR BEETS 0 0 3C,7G 4C,9G 2G 5G 0 0 0 0 3C,8G 9G     1C,3H 4C,8G 0 3G 0 0 VELVETLEAF 0 2G 2G 7G -- 0 0 0 0 0 0 3G 1C,4G 2C,5G     0 0 0 1C GIANT FOXTAIL 0 2G 8G 3C,9H 0 0 0 0 0 0 2C,5G 9H 4G 3C,7H 0 0 0     0 BARLEY 0 0 8G 3C,9G 0 7G 0 0 0 0 2C,8G 3C,9H 0 8G 0 0 0 0 DOWNY     BROME    CMPD 21 CMPD 22 CMPD 23 CMPD 24 CMPD 25 CMPD 26 CMPD 27 CMPD 28 C     MPD 29 CMPD 30 RATE = KG/HA 0.01 0.05 0.01 0.05 0.01 0.05  0.01 0.05     0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05 0.01 0.05       POSTEMERGENCE COTTON 4C,8H 5C,9G 0 2G 0 0 4C,9G 5C,9G 1H 2C,9H 3C,9G     3C,9H 9G 4C,9G 2G 3C,8G 0 0 3G 4G MORNING GLORY 5C,9H 10C 0 2C,3H 0 0 9C     9C 3C,6H 5C,9G 4C,9G 10C 4C,9H 4C,9H 5C,9G 10C 1C,3G 3C,7G 4C,9G 5C,9G     COCKLEBUR 2C,7G 5C,9H 2C 4C 0 0 9C 10C 3C,6H 3C,9H 4C,9G 9C 5C,9H 5C,9H     4C,9H 5C,9H 3C,8G 4C,9G 4C,9G 4C,9G NUTSEDGE 3C,9G 2C,9G 0 0 0 0 4C,9G     5C,9G 0 0 0 2C,6G 4G 9C 2G 9C 0 0 0 0 CRABGRASS 2C,7G 3C,9G 0 4G 0 0 0     3C,5G 0 0 0 0 0 2G 0 0 0 0 0 0 BARNYARD GRASS 9C 10C 0 2C,5H 0 3C,5H     3C,9H 5C,9G 0 2C,7G 1C,8G 4C,9G 3C,8H 9C 2C,5G 3C,8H 0 0 2C,5G 2C,3G     WILD OATS 5C,9G 9C 2C 4C,9G 0 3C,8G 5G 9G 0 0 3G 2C,6G 4C,9G 4C,9G 0     2C,3G 0 0 0 0 WHEAT 3C,9G 3C,9G 7G 3C,8G 0 6G 9G 9G 0 4G 7G 9G 9G 9G 0     6G 0 0 0 0 CORN 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 SOYBEAN 4C,8G     5C,9G 2C,5G 4C,9G 0 0 4C,9G 5C,9G 0 2C,2G 3C,8G 4C,9G 4C,8G 4C,9G 3C,9G     3C,8G 0 0 3C,8G 4C,9G RICE 4C,9G 6C,9G 2G 4C,8G 0 3C,7G 3C,8G 5C,9G 0 4G     5G 3C,7G 5C,9G 9C 3G 9G 0 0 0 5G SORGHUM 5C,9G 5C,9G 0 3C,4H 3C 4C,8H     4C,9G 9C 2C,6G 3C,7G 3C,8H 4C,9G 4C,9G 4C,9G 5G 3C,9G 0 1C,2G 0 4C,9G     CHEATGRASS 5C,9G 5C,9G 2G 8G 0 5G 6G 9G 0 4G 6G 2C,9G 9C 9C -- -- SUGAR     BEETS 5C,9H 9C 0 5H 0 2G 9C 9C 3C,7H 4C,9H 4C,9G 9C 5C,9H 9C 5C,9G 5C,9G     2C,7G 4C,8G 3C,7G 9C VELVETLEAF 3C,7H 4C,8H 2C,3G 2C,3H -- 0 5C,9G 9C 0     4G 3C,8H 7G 4C,8G 5C,9H 4G 4C,9H 0 2G 0 5G GIANT FOXTAIL 9C 10C 0 4G 0     2G 5G 3C,9G 0 2G 2G 3C,7G 2C,8G 5C,9G 0 0 0 0 0 0 BARLEY 4C,8G 5C,9G 2C     3C,8G 0 3C,5G 2C,8G 4C,9G 0 3G 5G 3C,7G 3C,9G 5C,9G 0 4G 0 0 0 2G DOWNY     BROME -- -- 2G 3C,8G 0 0 2C,5G 2C,6G PREEMERGENCE COTTON 2G 3C,9G 0 0 0     0 0 2H 0 0 0 1C 6G 6G 0 0 0 0 0 0 MORNING GLORY 1C,3H 9G 0 2C 0 0 0 9G 0     0 0 3C,8H 0 3G 1C 8G 0 0 0 3C,5H COCKLEBUR 5G 8H 0 0 0 0 1C 3C,3H 0 0 0     2C,6H 2G 2G 1C 3C,8H 0 3G 0 2C NUTSEDGE 2C,8G 10E 0 0 0 0 0 10E 0 0 0 0     4G 10E 0 7G 0 0 0 0 CRABGRASS 2C,7H 3C,9H 0 0 0 0 0 2G 0 0 0 0 0 2G 0 0     0 0 0 0 BARNYARD GRASS 0 4C,9H 0 0 0 0 2C,5G 7G 0 0 0 1H 2G 4G 0 3C,7H 0     0 0 0 WILD OATS 0 8G 0 0 0 0 0 1C 0 0 0 0 0 0 0 0 0 0 0 0 WHEAT 0 3C,9H     0 0 0 0 8G 2C,9H 0 0 5G 7G 0 0 0 2G 0 0 0 0 CORN 0 1C,3G 0 0 0 0 0 2G 0     0 0 0 0 2C 0 0 0 0 0 0 SOYBEAN 1C,2G 4C,8H 0 0 0 0 0 3C,4H 0 0 0 1C 3G     2C,5G 1C 3C,5H 0 0 0 2C,2G RICE 4G 4C,7G 0 0 0 2G 2G 4C,9G 0 0 0 6G     2C,2G 4C,8G 0 5G 0 0 0 0 SORGHUM 3C,6H 3C,9H 0 0 0 0 2C,5G 9H 0 2C 0     3C,7G 0 3C,7H 4G 2C,7H 0 0 0 5G CHEATGRASS 0 8G 0 2G 0 0 0 3G 0 0 0 0 2G     6G -- -- SUGAR BEETS 8G 5C,9G 0 0 0 0 7G 9G 0 5G 5G 3C,5G 5G 7G 7G 5C,9G     0 0 2G 3C,8G VELVETLEAF 2G 4C,8G 0 0 0 0 0 3C,5G 0 0 0 2G 5G 3C,8G 0 0 0     0 0 0 GIANT FOXTAIL 3C,9H 3C,9H 0 0 0 0 0 3G 0 0 0 2G 3G 3G 0 0 0 0 0 0     BARLEY 1C,6G 9G 0 0 0 0 6G 9G 0 0 0 2C,2G 0 2C,7G 0 5G 0 0 0 2G DOWNY     BROME -- -- 0 7G 0 0 0 3G       CMPD 31 CMPD 32 CMPD 33 CMPD 34 CMPD 35 CMPD 36 RATE = KG/HA 0.01 0.05 0     .01 0.05 0.01 0.05 0.01 0.05 0.05 2       POSTEMERGENCE COTTON 3C,8H 9H 3C,7H 4C,9H 0 0 2C,9G 9C 8H 0 MORNING     GLORY 4C,9G 5C,9G 3C,7H 5C,9G 0 2C,3H 4C,9G 9C 3C,9G 0 COCKLEBUR 7H     4C,9H 1H 2C,7G 2H 3G 7G 10C 3C,6G 0 NUTSEDGE 5C,9G 9G 3G 9G 0 0 9G 2C,8G     3C,8G 0 CRABGRASS 0 0 3G 3C,8G -- 0 3G 5G 3C,6G 0 BARNYARD GRASS 9C 9C     4C,9G 9C 0 2H 5C,9G 6C,9G 5C,9G 0 WILD OATS 2G 5G 3C,7G 3C,9G 0 0 9G     2C,9G 3C,9G 0 WHEAT 8G 4C,9G 9G 9C 0 8G 9G 2C,9G 2C,6G 0 CORN 0 0 0 0 0     0 5G 3C,7G 0 3G SOYBEAN 2G 3C,3G 2H,3G 3H,6G 0 2H 4C,9G 9C 3C,8H 0 RICE     4C,9G 9C 5C,9G 10C 0 6G 5C,9G 6C,9G 5C,9G 0 SORGHUM 4C,9G 5C,9G 4C,9G     4C,9G 0 0 4C,9G 5C,9G 4C,9G 0 CHEATGRASS 9G 5C,9G 9C 9C 0 4G 8G 9G 4C,9G     0 SUGAR BEETS 4C,9H 9C 9C 9C 0 7H 9C 9C 9C 0 VELVETLEAF 4C,9G 9C 3C,6H     3C,9H 1H 5G 5C,9G 5C,9G 3C,8H 0 GIANT FOXTAIL 3C,7G 4C,9G 4C,9G 9C -- 5G     4C,9G 5C,9G 3C,8G 0 BARLEY 8G 3C,8G 3C,9G 5C,9G 0 2C,5G 7G 2C,9G 4C,7G 0     DOWNY BROME PREEMERGENCE COTTON 0 0 0 4G 0 0 6G 8G 4G 0 MORNING GLORY 1H     2C,3H 0 4H 0 0 4H 8G 3C,3H 0 COCKLEBUR 0 0 0 0 0 0 1H 7G 0 0 NUTSEDGE 0     9G 0 10E 0 0 8G 10E 3C,8G 0 CRABGRASS 0 0 0 2G -- -- 0 0 9G 0 BARNYARD     GRASS 0 2C,7G 2C 9H 0 0 6G 3C,9H 3C,8H 0 WILD OATS 0 0 0 2C,3G 0 0 4G     2C,7G 2C,3G 0 WHEAT 0 6G 0 7H 0 0 5G 2C,8H 0 0 CORN 0 0 0 0 0 0 2C,2G     4C,5G 2C,2G 0 SOYBEAN 0 1H 0 4G 0 0 3H 3C,5H 3C,3H 0 RICE 0 3C,4G 0     3C,9G 0 0 9H 9H 9H 0 SORGHUM 2C,3G 4C,9G 2G 3C,8H 0 0 3C,8G 3C,9H 3C,8H     0 CHEATGRASS 0 6G 0 2C,8H 0 0 4G 7G 5G 0 SUGAR BEETS 7H 4C,8H 5G 3C,9G 0     2G 2C,8G 9G 8H 0 VELVETLEAF 2G 3G 0 3C,6H 0 0 2C,2H 8G 3G 0 GIANT     FOXTAIL 0 5G 0 2C,7H 0 0 2G 9H 3C,8G 0 BARLEY 0 7G 0 2C,7G 0 0 8G 8G 8G     0 DOWNY BROME

Test B Postemergence

Three round pans (25 cm diameter by 12.5 cm deep) were filled withSassafras sandy loam soil. One pan was planted with nutsedge (Cyperusrotundus) tubers, crabgrass (Digitaria sanguinalis). sicklepod (Cassiaobtusifolia), jimsonweed (Datura stramonium), velvetleaf (Abutilontheophrasti), lambsquarters (Chenopodium album), rice (Oryza sativa),and teaweed (Sida spinosa). The second pot was planted with greenfoxtail (Setaria viridis), cocklebur (Xanthium pensylvanicum),morningglory (Ipomoea hederacea), cotton (Gosspyoium hirsutum),johnsongrass (Sorghum halepense), barnyardgrass (Echinochloa crusgalli),corn (Zea mays), soybean (Glycine max), and giant foxtail (Setariafaberii). The third pot was planted with wheat (Triticum aestivum),barley (Hordeum vulgare), wild buckwheat (Polygonum convolvulus),cheatgrass (Bromus secalinus), sugarbeet (Beta vulgaris), wild oat(Avena fatua), viola (Viola arvensis), blackgrass (Alopecurusmyosuroides), and rape (Brassica napus). The plants were grown forapproximately fourteen days, then sprayed postemergence with thechemicals dissolved in a non-phytotoxic solvent.

Preemergence

Three round pans (25 cm diameter by 12.5 cm deep) were filled withSassafras sandy loam soil. One pan was planted with nutsedge tubers,crabgrass, sicklepod, jimsonweed, velvetleaf, lambsquarters, rice, andteaweed. The second pan was planted with green foxtail, cocklebur,morningglory, cotton, johnsongrass, barnyardgrass, corn, soybean, andgiant foxtail. The third pot was planted with wheat, barley, wildbuckwheat, cheatgrass, sugarbeet, wild oat, viola, blackgrass, and rape.The three pans were sprayed preemergence with the chemicals dissolved ina non-phytotoxic solvent.

Treated plants and controls were maintained in the greenhouse forapproximately 24 days, then all treated plants were compared to controlsand visually rated for plant response.

Response ratings are based on a scale of 0 to 100 where 0=no effect, and100=complete control. A dash (-) response means no test.

Response ratings are contained in Table B.

                                      TABLE B    __________________________________________________________________________                CMPD 1         CMPD 3         CMPD 6    RATE RATE = G/HA                0001                   0004                      0016                         0062                            0250                               0001                                  0004                                     0016                                        0062                                           0250                                              0001                                                 0004                                                    0016                                                       0062                                                          0250    __________________________________________________________________________    POSTEMERGENCE    GIANT FOXTAIL                30 50 70 100                            -- 30 50 80 -- -- 30 60 90 100                                                          --    VELVETLEAF  30 60 90 100                            -- 30 50 70 90 -- 30 50 70 90 --    SUGAR BEETS 50 70 100                         100                            -- 80 100                                     100                                        -- -- 70 90 100                                                       -- --    CRABGRASS   0  30 50 80 -- 30 50 70 90 -- 0  0  30 50 --    TEAWEED     30 50 70 90 -- 0  30 60 90 -- 0  30 50 70 --    JIMSONWEED  30 50 70 100                            -- 50 70 90 100                                           -- 30 50 70 100                                                          --    RICE        40 70 100                         100                            -- 50 100                                     100                                        100                                           -- 0  0  70 90 --    COCKLEBUR   0  0  30 70 -- 30 50 70 90 -- 0  30 60 90 --    COTTON      0  30 50 70 -- 0  30 50 70 -- 0  0  30 70 --    SOYBEAN     0  0  60 80 -- 30 50 80 -- -- 0  0  70 -- --    BARNYARD GRASS                30 60 100                         100                            -- 40 60 100                                        100                                           -- 30 60 90 100                                                          --    WILD OATS   0  0  30 70 -- 30 50 70 -- -- 0  0  50 -- --    MORNINGGLORY                30 60 90 100                            -- 30 50 70 90 -- 50 70 80 90 --    WHEAT       0  20 30 60 -- 30 50 70 -- -- 0  30 60 -- --    CASSIA      0  0  30 50 -- 30 50 70 100                                           -- 0  0  30 60 --    JOHNSONGRASS                30 60 100                         100                            -- 50 90 100                                        100                                           -- 30 50 70 90 --    NUTSEDGE    0  30 60 90 -- 30 60 90 100                                           -- 0  30 50 70 --    CORN        0  0  0  0  -- 0  0  0  -- -- 0  0  0  -- --    WILD BUCKWHEAT                0  30 50 80 -- 30 50 70 -- -- 0  0  30 -- --    BLACK GRASS 0  30 50 80 -- 0  0  30 -- -- 30 50 70 -- --    RAPESEED    70 100                      100                         100                            -- 90 100                                     100                                        -- -- 100                                                 100                                                    100                                                       -- --    BARLEY      0  30 60 100                            -- 30 60 80 -- -- 0  0  50 -- --    GREEN FOXTAIL                30 50 70 100                            -- 30 50 70 90 -- 30 50 70 100                                                          --    CHEAT GRASS 0  30 60 100                            -- 30 50 70 -- -- 0  30 60 -- --    BUCKWHEAT   -- -- -- -- -- -- -- -- -- -- -- -- -- -- --    VIOLA       -- -- -- -- -- 0  0  100                                        -- -- 50 70 100                                                       -- --    LAMBSQUARTER                50 70 90 100                            -- 50 70 90 100                                           -- 30 50 70 100                                                          --    PREEMERGENCE    GIANT FOXTAIL                -- 30 50 90 100                               -- 0  30 60 100                                              -- 0  30 70 90    VELVETLEAF  -- 0  30 60 90 -- 0  30 50 80 -- 0  30 70 90    SUGAR BEETS -- 30 50 70 90 -- 70 80 90 100                                              -- 30 60 80 90    CRABGRASS   -- 0  30 50 100                               -- 0  30 60 90 -- 0  0  30 60    TEAWEED     -- 0  30 50 80 -- 0  30 50 80 -- 0  30 50 80    JIMSONWEED  -- 0  30 60 90 -- 30 50 70 90 -- 0  30 60 90    RICE        -- 80 100                         100                            100                               -- 70 90 100                                           100                                              -- 30 70 100                                                          100    COCKLEBUR   -- 0  30 70 100                               -- 0  30 60 100                                              -- 0  30 50 90    COTTON      -- 0  20 40 60 -- 0  30 50 70 -- 0  0  30 60    SOYBEAN     -- 0  0  20 60 -- 0  30 70 90 -- 0  0  20 70    BARNYARD GRASS                -- 30 50 80 100                               -- 0  50 80 100                                              -- 0  50 70 90    WILD OATS   -- 0  0  30 60 -- 0  30 50 70 -- 0  0  30 60    MORNINGGLORY                -- 0  0  50 80 -- 30 50 70 90 -- 0  0  50 70    WHEAT       -- 0  20 30 60 -- 0  0  50 70 -- 0  20 40 80    CASSIA      -- 0  30 50 70 -- 0  30 60 90 -- 0  30 60 90    JOHNSONGRASS                -- 30 60 90 100                               -- 50 70 90 100                                              -- 0  50 80 90    NUTSEDGE    -- 0  30 50 100                               -- 0  0  30 90 -- 30 50 80 100    CORN        -- 0  0  0  0  -- 0  0  0  0  -- 0  0  0  0    WILD BUCKWHEAT                -- 30 50 70 90 -- 30 50 70 90 -- 30 50 80 90    BLACK GRASS -- 0  30 60 90 -- 30 50 70 100                                              -- 50 70 90 100    RAPESEED    -- 50 70 90 100                               -- 70 80 90 100                                              -- 40 60 80 100    BARLEY      -- 0  0  30 70 -- 0  0  50 90 -- 0  30 50 90    GREEN FOXTAIL                -- 30 50 90 100                               -- 50 80 100                                           100                                              -- 30 50 100                                                          100    CHEAT GRASS -- 0  30 50 80 -- 30 60 90 100                                              -- 0  30 70 90    BUCKWHEAT   -- -- -- -- -- -- -- -- -- -- -- -- -- -- --    VIOLA       -- -- -- -- -- -- 30 50 70 100                                              -- 30 60 80 100    LAMBSQUARTER                -- 30 60 100                            100                               -- 30 60 90 100                                              -- 50 70 80 90    __________________________________________________________________________                               CMPD 10     CMPD 12                   RATE RATE = G/HA                               0004                                  0016                                     0062                                        0250                                           0001                                              0004                                                 0016                                                    0062                                                       0250                                                          0.25    __________________________________________________________________________                   POSTEMERGENCE                   GIANT FOXTAIL                               0  50 60 -- 20 70 90 95 -- 10                   VELVETLEAF  20 60 80 -- -- 0  80 -- -- 0                   SUGAR BEETS 20 0  90 -- 30 100                                                 100                                                    100                                                       -- 20                   CRABGRASS   0  0  0  -- -- 50 60 80 -- 20                   TEAWEED     0  40 50 -- -- 20 50 70 -- 20                   JIMSONWEED  0  20 50 -- -- 50 50 85 -- 0                   RICE        0  50 90 -- -- 90 100                                                    100                                                       -- 40                   COCKLEBUR   0  50 70 -- 0  0  30 100                                                       -- 0                   COTTON      0  20 50 -- 20 70 80 85 -- 10                   SOYBEAN     0  40 70 -- 20 30 50 85 -- 10                   BARNYARD GRASS                               20 70 100                                        -- 60 100                                                 100                                                    100                                                       -- 50                   WILD OATS   0  70 20 -- 20 60 60 80 -- 20                   MORNINGGLORY                               30 40 80 -- 60 70 90 100                                                       -- 20                   WHEAT       0  40 60 -- 80 100                                                 100                                                    100                                                       -- 40                   CASSIA      0  30 60 -- -- 0  -- 100                                                       -- 0                   JOHNSONGRASS                               20 80 100                                        -- 60 100                                                 100                                                    100                                                       -- 50                   NUTSEDGE    0  0  40 -- -- 70 70 100                                                       -- 0                   CORN        0  30 50 -- 0  0  0  10 -- 0                   WILD BUCKWHEAT                               0  20 80 -- 0  0  70 90 -- 0                   BLACK GRASS 0  50 80 -- 40 70 80 100                                                       -- 30                   RAPESEED    0  100                                     100                                        -- 70 100                                                 100                                                    100                                                       -- 70                   BARLEY      0  30 70 -- 60 90 100                                                    100                                                       -- 20                   GREEN FOXTAIL                               0  30 60 -- 30 70 90 95 -- 20                   CHEAT GRASS 0  20 40 -- 50 80 70 100                                                       -- 20                   BUCKWHEAT   -- -- -- -- -- -- -- -- -- --                   VIOLA       0  30 50 -- 20 20 50 90 -- 20                   LAMBSQUARTER                               30 70 80 -- -- 50 80 95 -- 0                   PREEMERGENCE                   GIANT FOXTAIL                               -- 40 70 80 0  20 80 100                                                       100                                                          --                   VELVETLEAF  -- 20 50 90 0  0  10 85 80 --                   SUGAR BEETS -- 30 70 80 0  30 80 95 95 --                   CRABGRASS   -- 0  0  20 0  20 30 85 90 --                   TEAWEED     -- 0  60 90 0  20 0  80 95 --                   JIMSONWEED  -- 0  30 70 0  20 0  80 100                                                          --                   RICE        -- 50 90 100                                           10 60 80 -- -- --                   COCKLEBUR   -- 0  -- 50 0  20 20 70 80 --                   COTTON      -- 0  20 50 0  0  20 80 85 --                   SOYBEAN     -- 0  0  20 0  10 20 30 90 --                   BARNYARD GRASS                               -- 30 80 90 10 20 70 100                                                       100                                                          --                   WILD OATS   -- 0  0  20 20 30 50 60 70 --                   MORNINGGLORY                               -- 0  30 40 0  0  20 80 85 --                   WHEAT       -- 0  0  20 0  20 30 90 100                                                          --                   CASSIA      -- 0  20 70 -- -- -- -- -- --                   JOHNSONGRASS                               -- 60 100                                        100                                           65 60 100                                                    100                                                       100                                                          --                   NUTSEDGE    -- 0  0  30 0  0  80 90 100                                                          --                   CORN        -- 20 0  0  0  0  10 20 20 --                   WILD BUCKWHEAT                               -- 50 70 100                                           0  0  70 80 85 --                   BLACK GRASS -- 50 80 90 50 70 80 -- 95 --                   RAPESEED    -- 40 40 90 20 30 80 95 95 --                   BARLEY      -- 0  20 20 0  20 40 85 90 --                   GREEN FOXTAIL                               -- 20 60 90 30 80 90 100                                                       100                                                          --                   CHEAT GRASS -- 30 60 90 20 40 60 85 85 --                   BUCKWHEAT   -- -- -- -- -- -- -- -- -- --                   VIOLA       -- 70 60 90 -- -- -- -- -- --                   LAMBSQUARTER                               -- 20 80 90 0  0  70 -- 95 --    __________________________________________________________________________

Test C Corn & Sorghum Test Postemergence

Six round containers (18 cm diameter) were filled with Sassafras sandyloam soil. One container was planted with corn and a second containerwith soybeans. Two containers were planted with the grass speciessorghum (Sorghum bicolor), green foxtail (Setaria viridis), johnsongrass(Sorghum halepense), barnyardgrass (Echinochloa crusgalli), fall panicum(Panicum dichotomiflorum), crabgrass (Digitaria sanguinalis) andnutsedge (Cyperus rotundus). Two containers were planted with thebroadleaf species cocklebur (Xanthium pensylvanicum), morningglory(Ipomoea hederacea), velvetleaf (Abutilon theophrasti), jimsonweed(Datura stramonium), ragweed (Ambrosia artemisifolia), lambsquarters(Chenopodium album), pigweed (Amaranthjus retroflexus), and smartweed(Polygonum pensylvanicum). The plants were grown 10-21 days, dependenton the species and then sprayed postemergence with the chemicalsdissolved in a non-phytotoxic solvent.

Preemergence

Six round containers (18 cm diameter) were filled with Tama silt loamsoil. The same species described in the postemergence section wereplanted and sprayed with the chemicals dissolved in a nonphytotoxicsolvent.

Evaluations

Treated plants and controls were maintained in the greenhouse forapproximately 28 days. Treated plants were then compared with controlplants and rated or plant response.

Response ratings are based on a scale of 0 to 100, where 0=no effect,and 100=complete control. A dash (-) response means no test. The resultsare in Table C.

                                      TABLE C    __________________________________________________________________________                CMPD 3               CMPD 6    RATE RATE GM/HA                0002                   0004                      0008                         0016                            0031                               0062                                  0125                                     0002                                        0004                                           0008                                              0016    __________________________________________________________________________    POSTEMERGENCE    CORN        0  0  0  0  0  0  20 -- 0  0  0    SOYBEAN     80 95 100                         100                            100                               100                                  100                                     -- 0  40 80    GREEN FXTL  50 70 85 95 100                               100                                  100                                     -- 0  0  25    GIANT FXTL  45 70 85 95 100                               100                                  100                                     -- 0  30 50    PANICUM     70 85 95 100                            100                               100                                  100                                     -- 0  20 40    CRABGRASS   0  0  0  30 50 75 95 -- 0  0  0    BARNYARDGRASS                90 100                      100                         100                            100                               100                                  100                                     -- 90 100                                              100    JOHNSONGRASS                100                   100                      100                         100                            100                               100                                  100                                     -- 95 100                                              100    SORGHUM     90 95 100                         100                            100                               100                                  100                                     -- 90 100                                              100    NUTSEDGE    35 70 85 95 95 100                                  100                                     -- 0  20 55    VELVETLEAF  30 45 65 70 85 90 100                                     -- 0  0  25    COCKLEBUR   80 90 100                         100                            100                               100                                  100                                     -- 0  35 65    SMARTWEED   35 50 80 95 100                               100                                  100                                     -- 40 60 70    LAMBSQUARTER                60 70 90 95 100                               100                                  100                                     -- 0  0  25    PIGWEED     90 100                      100                         100                            100                               100                                  100                                     -- 60 65 85    MORNINGGLORY                70 85 95 100                            100                               100                                  100                                     -- 0  30 60    JIMSONWEED  55 70 90 100                            100                               100                                  100                                     -- 35 50 --    RAGWEED     -- -- -- -- -- -- -- -- -- -- --    CORN ERLY INJ                -- -- -- -- -- -- -- -- -- -- --    PREEMERGENCE    CORN        -- -- -- 0  0  0  0  -- -- -- --    SOYBEAN     -- -- -- 0  0  0  0  -- -- -- --    GREEN FXTL  -- -- -- 0  20 40 65 -- -- -- --    GIANT FXTL  -- -- -- 0  25 40 60 -- -- -- --    PANICUM     -- -- -- 35 60 95 100                                     -- -- -- --    CRABGRASS   -- -- -- 0  0  0  20 -- -- -- --    BARNYARDGRASS                -- -- -- 0  0  30 65 -- -- -- --    JOHNSONGRASS                -- -- -- 0  35 65 80 -- -- -- --    SORGHUM     -- -- -- 0  20 65 100                                     -- -- -- --    NUTSEDGE    -- -- -- 0  0  0  40 -- -- -- --    VELVETLEAF  -- -- -- 0  0  0  0  -- -- -- --    COCKLEBUR   -- -- -- 0  0  0  0  -- -- -- --    SMARTWEED   -- -- -- 0  25 60 90 -- -- -- --    LAMBSQUARTER                -- -- -- 20 40 65 85 -- -- -- --    PIGWEED     -- -- -- 20 35 65 90 -- -- -- --    MORNINGGLORY                -- -- -- 0  0  0  0  -- -- -- --    JIMSONWEED  -- -- -- 0  0  0  35 -- -- -- --    RAGWEED     -- -- -- -- -- -- -- -- -- -- --    CORN ERLY INJ                -- -- -- -- -- -- -- -- -- -- --    __________________________________________________________________________                CMPD 6     CMPD 12    RATE RATE GM/HA                0031                    0062                       0125                           0002                              0004                                 0008                                    0016                                       0031                                          0062                                             0125    __________________________________________________________________________    POSTEMERGENCE    CORN        0   0  0   0  0  0  0  0  0  0    SOYBEAN     100 100                       100 0  0  25 50 75 95 100    GREEN FXTL  35  75 100 40 70 90 100                                       100                                          100                                             100    GIANT FXTL  85  100                       100 45 75 100                                    100                                       100                                          100                                             100    PANICUM     60  90 95  35 70 100                                    100                                       100                                          100                                             100    CRABGRASS   0   35 40  0  0  30 50 75 100                                             100    BARNYARDGRASS                100 100                       100 85 100                                 100                                    100                                       100                                          100                                             100    JOHNSONGRASS                100 100                       100 90 100                                 100                                    100                                       100                                          100                                             100    SORGHUM     100 100                       100 100                              100                                 100                                    100                                       100                                          100                                             100    NUTSEDGE    65  75 100 20 45 70 85 95 100                                             100    VELVETLEAF  50  70 85  0  35 45 65 80 100                                             100    COCKLEBUR   85  95 100 0  0  30 50 65 80 100    SMARTWEED   85  95 100 50 50 90 95 100                                          100                                             100    LAMBSQUARTER                40  65 80  0  0  25 55 75 90 95    PIGWEED     100 100                       100 75 100                                 100                                    100                                       100                                          100                                             100    MORNINGGLORY                75  80 90  60 85 95 100                                       100                                          100                                             100    JIMSONWEED  --  -- --  35 65 85 95 100                                          100                                             100    RAGWEED     --  -- --  -- -- -- -- -- -- --    CORN ERLY INJ                --  -- --  -- -- -- -- -- -- --    PREEMERGENCE    CORN        0   0  0   -- -- -- 0  0  0  0    SOYBEAN     0   0  0   -- -- -- 0  0  0  0    GREEN FXTL  0   20 55  -- -- -- 0  20 60 90    GIANT FXTL  0   20 60  -- -- -- 0  20 60 95    PANICUM     0   30 75  -- -- -- 40 70 95 100    CRABGRASS   0   0  0   -- -- -- 0  0  25 45    BARNYARDGRASS                0   25 40  -- -- -- 0  0  40 75    JOHNSONGRASS                0   60 100 -- -- -- 45 80 100                                             100    SORGHUM     0   50 80  -- -- -- 30 70 95 100    NUTSEDGE    0   0  30  -- -- -- 0  25 60 85    VELVETLEAF  0   0  35  -- -- -- 0  0  0  0    COCKLEBUR   0   0  0   -- -- -- 0  0  0  0    SMARTWEED   0   35 70  -- -- -- 0  30 80 100    LAMBSQUARTER                0   25 45  -- -- -- 0  20 65 85    PIGWEED     0   25 55  -- -- -- 0  35 80 100    MORNINGGLORY                0   0  20  -- -- -- 0  0  0  0    JIMSONWEED  0   0  40  -- -- -- 0  0  0  40    RAGWEED     --  -- --  -- -- -- -- -- -- --    CORN ERLY INJ                --  -- --  -- -- -- -- -- -- --    __________________________________________________________________________

Test D

POSTEMERGENCE GRASS CONTROL IN CORN

Johnsongrass (Sorghum halepense), shattercane (Sorghum bicolor), giantfoxtail (Setaria faberii), quackgrass (Agropyron repens) andbarnyardgrass (Echinochloa crusgalli) were planted in 5" standard potsfilled with Tama soil. Corn was planted in 7" pots filled with the samesoil. When the corn was 12 days old, the shattercane, giant foxtail andbarnyardgrass 14 days old, the johnsongrass 26 days old and thequackgrass 34 days old, they were all treated postemergence with theexperimental material dissolved in a proprietary solvent. Twenty-threedays after treatment, visual evaluation of plant injury was made. Theresults are shown in Table D.

                                      TABLE D    __________________________________________________________________________    POSTEMERGENCE                Compound 12    Rate g/ha   .5                  1 2 4  8   16 31 62 125    __________________________________________________________________________    Quackgrass  50                  80                    90                      100                         100 100                                100                                   100                                      100    Giant Foxtail                30                  40                    65                      85 95  100                                100                                   100                                      100    Shattercane 30                  60                    70                      75 90  95 100                                   100                                      100    Barnyardgrass                30                  50                    60                      85 100 100                                100                                   100                                      100    Johnsongrass                40                  50                    50                      80 95  100                                100                                   100                                      100    Corn        0 0 0 0  0   0  0  0  20    __________________________________________________________________________

What is claimed is:
 1. A compound selected from: ##STR23## wherein R₁ isH or C_(1-C) ₃ alkyl;R₂ is C₁ -C₃ alkyl or C₁ -C₂ alkoxy; or R₁ and R₂may be taken together to form --(CH₂)_(n) --, wherein n is 2, 3 or 4; R₃is H, Cl, F, Br, CH₃, CF₃, OCH₃, OCH₂ CH₃, OCF₂ H, SCH₃, SCH₂ CH₃, SCF₂H, NHR₄ or NR₄ R₅ ; R₄ is CH₃ or CH₂ CH₃ ; and R₅ is CH₃, CH₂ CH₃, OCH₃or OCH₂ CH₃.
 2. The compound of claim 1 wherein R₁ and R₂ are CH₃ and R₃is H.
 3. The compound of claim 1 which is2-(chlorosulfonyl)-N,N,-dimethyl-3-pyridinecarboxamide.